1-BROMO-4-BUTYLTHIOBENZENE

反应条件: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a solution of 4-bromophenyl n-butyl sulfide (1.5 g, 6.12 mmol) in 60 ml of dry THF was added nBuLi (4.1 ml, 1.6 M in hexanes) at −78° C. under nitrogen. The mixture was stirred for 1 hour at −78° C. and then DMF (2.0 ml) was added. The reaction mixture was stirred at room temperature for 2 hours. Then 40 ml of water was added to this mixture, the product was extracted three times by ether (3×50 ml) and the combined organic layer was dried over magnesium sulfate. After removal of solvent under reduced pressure, the product was purified by flash chromatography column using 10% of ethyl acetate in hexanes as eluant and isolated in 66.7% (0.88 g) yield.1H NMR (CDCl3, 500 MHz) δppm: 9.98 (s, 1H, CHO), 7.77 (d, J=8.5 Hz, 2H), 7.36 (d, J=8.5 Hz, 2H,), 7.11 (s, 2H), 3.02 (t, J=7.2 Hz, 2H, CH2), 1.71 (m, 2H, CH2), 1.50 (m, 2H, CH2), 0.97 (t, J=7.5 Hz, 6H, CH3). The reaction mixture was stirred at room temperature for 2 hours the product was extracted three times by ether (3×50 ml) the combined organic layer was dried over magnesium sulfate After removal of solvent under reduced pressure the product was purified by flash chromatography column isolated in 66.7% (0.88 g) yield

反应条件: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a solution of 4-bromophenyl n-butyl sulfide (1.5 g, 6.12 mmol) in 60 ml of dry THF was added nBuLi (4.1 ml, 1.6 M in hexanes) at −78° C. under nitrogen. The mixture was stirred for 1 hour at −78° C. and then DMF (2.0 ml) was added. The reaction mixture was stirred at room temperature for 2 hours. Then 40 ml of water was added to this mixture, the product was extracted three times by ether (3×50 ml) and the combined organic layer was dried over magnesium sulfate. After removal of solvent under reduced pressure, the product was purified by flash chromatography column using 10% of ethyl acetate in hexanes as eluant and isolated in 66.7% (0.88 g) yield.1H NMR (CDCl3, 500 MHz) δppm: 9.98 (s, 1H, CHO), 7.77 (d, J=8.5 Hz, 2H), 7.36 (d, J=8.5 Hz, 2H,), 7.11 (s, 2H), 3.02 (t, J=7.2 Hz, 2H, CH2), 1.71 (m, 2H, CH2), 1.50 (m, 2H, CH2), 0.97 (t, J=7.5 Hz, 6H, CH3). The reaction mixture was stirred at room temperature for 2 hours the product was extracted three times by ether (3×50 ml) the combined organic layer was dried over magnesium sulfate After removal of solvent under reduced pressure the product was purified by flash chromatography column isolated in 66.7% (0.88 g) yield

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

实验步骤: 4-Bromobenzenethiol (5 g, 26.44 mmol) was added to a solution of sodium methoxide (1.43 g, 26.48 mmol) in 20 ml of anhydrous methanol. The mixture was stirred for 30 min under nitrogen at room temperature and a solution of methyl iodide (4.51 g, 31.77 mmol) in 20 ml anhydrous methanol was then added. The reaction mixture was stirred overnight at room temperature, poured into 2 M of NaOH aqueous solution (30 ml) and extracted three times with ether (3×100 ml ). The combined organic layer was washed with saturated sodium chloride solution and dried over anhydrous magnesium sulfate. After removal of solvent, the product was purified by distillation at 117-119° C. (0.5 mmHg) and was isolated in 88.4% (5.72 g) yield. The reaction mixture was stirred overnight at room temperature extracted three times with ether (3×100 ml ) The combined organic layer was washed with saturated sodium chloride solution dried over anhydrous magnesium sulfate After removal of solvent the product was purified by distillation at 117-119° C. (0.5 mmHg) was isolated in 88.4% (5.72 g) yield

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

实验步骤: 4-Bromobenzenethiol (5 g, 26.44 mmol) was added to a solution of sodium methoxide (1.43 g, 26.48 mmol) in 20 ml of anhydrous methanol. The mixture was stirred for 30 min under nitrogen at room temperature and a solution of methyl iodide (4.51 g, 31.77 mmol) in 20 ml anhydrous methanol was then added. The reaction mixture was stirred overnight at room temperature, poured into 2 M of NaOH aqueous solution (30 ml) and extracted three times with ether (3×100 ml ). The combined organic layer was washed with saturated sodium chloride solution and dried over anhydrous magnesium sulfate. After removal of solvent, the product was purified by distillation at 117-119° C. (0.5 mmHg) and was isolated in 88.4% (5.72 g) yield. The reaction mixture was stirred overnight at room temperature extracted three times with ether (3×100 ml ) The combined organic layer was washed with saturated sodium chloride solution dried over anhydrous magnesium sulfate After removal of solvent the product was purified by distillation at 117-119° C. (0.5 mmHg) was isolated in 88.4% (5.72 g) yield

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

实验步骤: The general procedure was used to convert 4-iodo bromobenzene and n-butyl sulfide to the title product. Purification by flash chromatography (hexane as the eluent) gave the analytically pure product as a clear oil (450 mg, 92% yield). 1H NMR (300 MHz, CDCl3) δ 7.39–7.36 (d, J=8.6, 2H; Ha, Ha′), 7.19–7.15 (d, J=8.28, 2H; Hb, Hb′), 2.91–2.86 (t, J=7.1, 2H; Hc), 1.57–1.47 (m, 2H; Hd), 1.41–1.31 (m, 2H; He), 0.94–0.89 (t, J=7.3, 3H; Hf). 13C NMR (75 MHz, CDCl3) δ 136.2 (C4), 131.7 (C1, C1′), 130.2 (C2, C2′), 119.2 (C3), 33.2 (C5), 30.9 (C6), 21.8 (C7), 13.5 (C8). Anal. Calcd. for C10H13Br C, 48.99; H, 5.34; S, 13.08; Found C, 49.09; H, 5.44; S, 12.96.

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

实验步骤: The general procedure was used to convert 4-iodo bromobenzene and n-butyl sulfide to the title product. Purification by flash chromatography (hexane as the eluent) gave the analytically pure product as a clear oil (450 mg, 92% yield). 1H NMR (300 MHz, CDCl3) δ 7.39–7.36 (d, J=8.6, 2H; Ha, Ha′), 7.19–7.15 (d, J=8.28, 2H; Hb, Hb′), 2.91–2.86 (t, J=7.1, 2H; Hc), 1.57–1.47 (m, 2H; Hd), 1.41–1.31 (m, 2H; He), 0.94–0.89 (t, J=7.3, 3H; Hf). 13C NMR (75 MHz, CDCl3) δ 136.2 (C4), 131.7 (C1, C1′), 130.2 (C2, C2′), 119.2 (C3), 33.2 (C5), 30.9 (C6), 21.8 (C7), 13.5 (C8). Anal. Calcd. for C10H13Br C, 48.99; H, 5.34; S, 13.08; Found C, 49.09; H, 5.44; S, 12.96.

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

实验步骤: n-Butyllithium (6.8 ml, 10.0M in hexane, 0.068 mol) was added to a stirred, cooled (-78° C.) solution of compound 1 (16.56 g, 0.067 mol) in dry THF (200 ml), under dry nitrogen at -78° C. The mixture was maintained under these conditions for a further 0.5 h (glc analysis confirmed a complete reaction) before being poured into a slurry of `Cardice` and dry THF. The mixture was allowed to warm to room temperature overnight. The combined organic extracts were evaporated in vacuo and the residue was dissolved in boiling acetic acid. Ice (400 g) was added to the solution and the product was filtered off and dried in vacuo (KOH, P2O5). at -78° C The mixture was maintained under these conditions for a further 0.5 h (glc analysis a complete reaction) The combined organic extracts were evaporated in vacuo the residue was dissolved Ice (400 g) was added to the solution the product was filtered off dried in vacuo (KOH, P2O5)