2,6-二氯-4-甲基苯甲酰基 氯化物

反应条件: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: An ambient temperature solution of 2,6-dichloro-4-methylbenzoyl chloride (5.5 g, 25 mmol) in benzene (30 ml) was treated in portions with aluminum chloride (3.45 g, 25.9 mmol). When hydrogen chloride evolution ceased, the mixture was heated at 80° C. for 15 hours. The mixture was cooled, quenched by addition of ice and concentrated hydrochloric acid (5 ml), and diluted with diethyl ether (50 ml). The layers were separated and the organic phase washed with water, dried over anhydrous magnesium sulfate, and evaporated to dryness under vacuum. The semisolid residue was chromatographed on a column of silica gel (300 g) eluted with 4:1 (v/v) hexanedichloromethane to provide 4.60 g (69%) 2,6-dichloro-4-methylbenzophenone, m.p. 75.5°-76.5° C. The mixture was cooled quenched by addition of ice and concentrated hydrochloric acid (5 ml) diluted with diethyl ether (50 ml) The layers were separated the organic phase washed with water dried over anhydrous magnesium sulfate evaporated to dryness under vacuum The semisolid residue was chromatographed on a column of silica gel (300 g) eluted with 4:1 (v/v) hexanedichloromethane

反应条件: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: An ambient temperature solution of 2,6-dichloro-4-methylbenzoyl chloride (5.5 g, 25 mmol) in benzene (30 ml) was treated in portions with aluminum chloride (3.45 g, 25.9 mmol). When hydrogen chloride evolution ceased, the mixture was heated at 80° C. for 15 hours. The mixture was cooled, quenched by addition of ice and concentrated hydrochloric acid (5 ml), and diluted with diethyl ether (50 ml). The layers were separated and the organic phase washed with water, dried over anhydrous magnesium sulfate, and evaporated to dryness under vacuum. The semisolid residue was chromatographed on a column of silica gel (300 g) eluted with 4:1 (v/v) hexanedichloromethane to provide 4.60 g (69%) 2,6-dichloro-4-methylbenzophenone, m.p. 75.5°-76.5° C. The mixture was cooled quenched by addition of ice and concentrated hydrochloric acid (5 ml) diluted with diethyl ether (50 ml) The layers were separated the organic phase washed with water dried over anhydrous magnesium sulfate evaporated to dryness under vacuum The semisolid residue was chromatographed on a column of silica gel (300 g) eluted with 4:1 (v/v) hexanedichloromethane

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A solution of 2,6-dichloro-4methylbenzoic acid (7.15 g, 34.9 mmol) in thionyl chloride (133 ml) containing dimethylformamide (1.3 ml) was refluxed 3 hours, evaporated under vacuum, and azeotroped twice with benzene. The residue was triturated with petroleum ether (b.p. 30°-60° C., 200 ml) and filtered. The filtrate was evaporated under vacuum to provide 8.5 g (109% of theory) 2,6-dichloro-4-methylbenzoyl chloride, IR (neat): 1785 cm-1. The crude chloride and chlorobenzene (94 g) were stirred in carbon tetrachloride (235 ml), treated in portions with aluminum chloride (5.35 g, 40.1 mmol), kept 30 minutes at ambient temperature, and refluxed 3 hours. The mixture was cooled, quenched by addition of ice and concentrated hydrochloric acid, and extracted three times with dichloromethane. The combined extracts were washed with water, dried over anhydrous magnesium sulfate, and evaporated under vacuum. The residue was chromatographed on a column of silica gel (400 g) eluted with 3:2 (v/v) dichloromethane-hexane to provide 7.19 g (69%) of 4-(4-chlorobenzoyl)-3,5-dichlorotoluene, m.p. 111.5°-114° C. was refluxed 3 hours evaporated under vacuum azeotroped twice with benzene The residue was triturated with petroleum ether (b.p. 30°-60° C., 200 ml) filtered The filtrate was evaporated under vacuum

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A solution of 2,6-dichloro-4methylbenzoic acid (7.15 g, 34.9 mmol) in thionyl chloride (133 ml) containing dimethylformamide (1.3 ml) was refluxed 3 hours, evaporated under vacuum, and azeotroped twice with benzene. The residue was triturated with petroleum ether (b.p. 30°-60° C., 200 ml) and filtered. The filtrate was evaporated under vacuum to provide 8.5 g (109% of theory) 2,6-dichloro-4-methylbenzoyl chloride, IR (neat): 1785 cm-1. The crude chloride and chlorobenzene (94 g) were stirred in carbon tetrachloride (235 ml), treated in portions with aluminum chloride (5.35 g, 40.1 mmol), kept 30 minutes at ambient temperature, and refluxed 3 hours. The mixture was cooled, quenched by addition of ice and concentrated hydrochloric acid, and extracted three times with dichloromethane. The combined extracts were washed with water, dried over anhydrous magnesium sulfate, and evaporated under vacuum. The residue was chromatographed on a column of silica gel (400 g) eluted with 3:2 (v/v) dichloromethane-hexane to provide 7.19 g (69%) of 4-(4-chlorobenzoyl)-3,5-dichlorotoluene, m.p. 111.5°-114° C. was refluxed 3 hours evaporated under vacuum azeotroped twice with benzene The residue was triturated with petroleum ether (b.p. 30°-60° C., 200 ml) filtered The filtrate was evaporated under vacuum

反应条件: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: An ambient temperature solution of 2,6-dichloro-4-methylbenzoyl chloride (5.5 g, 25 mmol) in benzene (30 ml) was treated in portions with aluminum chloride (3.45 g, 25.9 mmol). When hydrogen chloride evolution ceased, the mixture was heated at 80° C. for 15 hours. The mixture was cooled, quenched by addition of ice and concentrated hydrochloric acid (5 ml), and diluted with diethyl ether (50 ml). The layers were separated and the organic phase washed with water, dried over anhydrous magnesium sulfate, and evaporated to dryness under vacuum. The semisolid residue was chromatographed on a column of silica gel (300 g) eluted with 4:1 (v/v) hexanedichloromethane to provide 4.60 g (69%) 2,6-dichloro-4-methylbenzophenone, m.p. 75.5°-76.5° C. The mixture was cooled quenched by addition of ice and concentrated hydrochloric acid (5 ml) diluted with diethyl ether (50 ml) The layers were separated the organic phase washed with water dried over anhydrous magnesium sulfate evaporated to dryness under vacuum The semisolid residue was chromatographed on a column of silica gel (300 g) eluted with 4:1 (v/v) hexanedichloromethane

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A solution of 2,6-dichloro-4methylbenzoic acid (7.15 g, 34.9 mmol) in thionyl chloride (133 ml) containing dimethylformamide (1.3 ml) was refluxed 3 hours, evaporated under vacuum, and azeotroped twice with benzene. The residue was triturated with petroleum ether (b.p. 30°-60° C., 200 ml) and filtered. The filtrate was evaporated under vacuum to provide 8.5 g (109% of theory) 2,6-dichloro-4-methylbenzoyl chloride, IR (neat): 1785 cm-1. The crude chloride and chlorobenzene (94 g) were stirred in carbon tetrachloride (235 ml), treated in portions with aluminum chloride (5.35 g, 40.1 mmol), kept 30 minutes at ambient temperature, and refluxed 3 hours. The mixture was cooled, quenched by addition of ice and concentrated hydrochloric acid, and extracted three times with dichloromethane. The combined extracts were washed with water, dried over anhydrous magnesium sulfate, and evaporated under vacuum. The residue was chromatographed on a column of silica gel (400 g) eluted with 3:2 (v/v) dichloromethane-hexane to provide 7.19 g (69%) of 4-(4-chlorobenzoyl)-3,5-dichlorotoluene, m.p. 111.5°-114° C. was refluxed 3 hours evaporated under vacuum azeotroped twice with benzene The residue was triturated with petroleum ether (b.p. 30°-60° C., 200 ml) filtered The filtrate was evaporated under vacuum

反应条件: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: An ambient temperature solution of 2,6-dichloro-4-methylbenzoyl chloride (5.5 g, 25 mmol) in benzene (30 ml) was treated in portions with aluminum chloride (3.45 g, 25.9 mmol). When hydrogen chloride evolution ceased, the mixture was heated at 80° C. for 15 hours. The mixture was cooled, quenched by addition of ice and concentrated hydrochloric acid (5 ml), and diluted with diethyl ether (50 ml). The layers were separated and the organic phase washed with water, dried over anhydrous magnesium sulfate, and evaporated to dryness under vacuum. The semisolid residue was chromatographed on a column of silica gel (300 g) eluted with 4:1 (v/v) hexanedichloromethane to provide 4.60 g (69%) 2,6-dichloro-4-methylbenzophenone, m.p. 75.5°-76.5° C. The mixture was cooled quenched by addition of ice and concentrated hydrochloric acid (5 ml) diluted with diethyl ether (50 ml) The layers were separated the organic phase washed with water dried over anhydrous magnesium sulfate evaporated to dryness under vacuum The semisolid residue was chromatographed on a column of silica gel (300 g) eluted with 4:1 (v/v) hexanedichloromethane

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A solution of 2,6-dichloro-4methylbenzoic acid (7.15 g, 34.9 mmol) in thionyl chloride (133 ml) containing dimethylformamide (1.3 ml) was refluxed 3 hours, evaporated under vacuum, and azeotroped twice with benzene. The residue was triturated with petroleum ether (b.p. 30°-60° C., 200 ml) and filtered. The filtrate was evaporated under vacuum to provide 8.5 g (109% of theory) 2,6-dichloro-4-methylbenzoyl chloride, IR (neat): 1785 cm-1. The crude chloride and chlorobenzene (94 g) were stirred in carbon tetrachloride (235 ml), treated in portions with aluminum chloride (5.35 g, 40.1 mmol), kept 30 minutes at ambient temperature, and refluxed 3 hours. The mixture was cooled, quenched by addition of ice and concentrated hydrochloric acid, and extracted three times with dichloromethane. The combined extracts were washed with water, dried over anhydrous magnesium sulfate, and evaporated under vacuum. The residue was chromatographed on a column of silica gel (400 g) eluted with 3:2 (v/v) dichloromethane-hexane to provide 7.19 g (69%) of 4-(4-chlorobenzoyl)-3,5-dichlorotoluene, m.p. 111.5°-114° C. was refluxed 3 hours evaporated under vacuum azeotroped twice with benzene The residue was triturated with petroleum ether (b.p. 30°-60° C., 200 ml) filtered The filtrate was evaporated under vacuum