(7-溴-2,3-二氢苯并[B][1,4]二氧杂环己烯-2-基)甲醇

反应条件: temp:140.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 4 batches of a mixture of (7-bromo-2,3-dihydro-1,4-benzodioxin-2-yl)methanol (0.5 g, 2.0 mmol), sodium methanesulfinate (85%) (0.37 g, 3.1 mmol), CuI (0.039 g, 0.2 mmol), L-proline (0.047 g, 0.4 mmol) and K2CO3 (0.056 g, 0.4 mmol) in DMSO (4 ml) was heated under microwave radiation to 140° C. for 1 h in a nitrogen-flushed vial. The batches were mixed and diluted with water and HCl (1 N). The resulting solution was extracted with EtOAc. The combined organic phases were washed with brine, dried and purified on flash column chromatography (isooctane/EtOAc/MeOH) to give the title compound (0.89 g). MS m/z (rel. intensity, 70 eV) 244 (M+, bp), 213 (40), 165 (27), 134 (22), 79 (18). flushed vial The batches were mixed diluted with water and HCl (1 N) The resulting solution was extracted with EtOAc The combined organic phases were washed with brine dried purified on flash column chromatography (isooctane/EtOAc/MeOH)

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

实验步骤: 5-bromo-2-(oxiran-2-ylmethoxy)phenyl formate (12.6 g, 46.0 mmol) was dissolved in dioxane (50 ml) and KOH (10%)/NaOH (20%) was added. Water and EtOAc was added and the phases were separated. The combined organic phases were washed with brine and dried to give the title compound (10.3 g). MS m/z (rel. intensity, 70 eV) 245 (M+, 96) 244 (M+, bp), 213 (29), 189 (46), 188 (49). the phases were separated The combined organic phases were washed with brine dried

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a stirred solution of 5-bromosalicylaldehyde (5.0 g, 24.9 mmol), and epichlorohydrin (5.6 mL, 72.1 mmol) in 20 mL of DMF at 80° C. was added K2CO3 slowly in portions. The resulting mixture was then heated at 90° C. for 3 h. Reaction was then stopped, water was added, extracted with diethyl ether. The organic extracts were washed with water, brine, dried over Na2SO4, concentrated in vacuo. The residue was purified on a SiO2 flash column chromatography eluting with 15-30% EtOAc/hexanes to give 2.82 g (44%) of the title compound as colorless oil. Reaction extracted with diethyl ether The organic extracts were washed with water, brine dried over Na2SO4 concentrated in vacuo The residue was purified on a SiO2 flash column chromatography eluting with 15-30% EtOAc/hexanes

反应条件: temp:140.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 4 batches of a mixture of (7-bromo-2,3-dihydro-1,4-benzodioxin-2-yl)methanol (0.5 g, 2.0 mmol), sodium methanesulfinate (85%) (0.37 g, 3.1 mmol), CuI (0.039 g, 0.2 mmol), L-proline (0.047 g, 0.4 mmol) and K2CO3 (0.056 g, 0.4 mmol) in DMSO (4 ml) was heated under microwave radiation to 140° C. for 1 h in a nitrogen-flushed vial. The batches were mixed and diluted with water and HCl (1 N). The resulting solution was extracted with EtOAc. The combined organic phases were washed with brine, dried and purified on flash column chromatography (isooctane/EtOAc/MeOH) to give the title compound (0.89 g). MS m/z (rel. intensity, 70 eV) 244 (M+, bp), 213 (40), 165 (27), 134 (22), 79 (18). flushed vial The batches were mixed diluted with water and HCl (1 N) The resulting solution was extracted with EtOAc The combined organic phases were washed with brine dried purified on flash column chromatography (isooctane/EtOAc/MeOH)

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

实验步骤: 5-bromo-2-(oxiran-2-ylmethoxy)phenyl formate (12.6 g, 46.0 mmol) was dissolved in dioxane (50 ml) and KOH (10%)/NaOH (20%) was added. Water and EtOAc was added and the phases were separated. The combined organic phases were washed with brine and dried to give the title compound (10.3 g). MS m/z (rel. intensity, 70 eV) 245 (M+, 96) 244 (M+, bp), 213 (29), 189 (46), 188 (49). the phases were separated The combined organic phases were washed with brine dried

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:140.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 4 batches of a mixture of (7-bromo-2,3-dihydro-1,4-benzodioxin-2-yl)methanol (0.5 g, 2.0 mmol), sodium methanesulfinate (85%) (0.37 g, 3.1 mmol), CuI (0.039 g, 0.2 mmol), L-proline (0.047 g, 0.4 mmol) and K2CO3 (0.056 g, 0.4 mmol) in DMSO (4 ml) was heated under microwave radiation to 140° C. for 1 h in a nitrogen-flushed vial. The batches were mixed and diluted with water and HCl (1 N). The resulting solution was extracted with EtOAc. The combined organic phases were washed with brine, dried and purified on flash column chromatography (isooctane/EtOAc/MeOH) to give the title compound (0.89 g). MS m/z (rel. intensity, 70 eV) 244 (M+, bp), 213 (40), 165 (27), 134 (22), 79 (18). flushed vial The batches were mixed diluted with water and HCl (1 N) The resulting solution was extracted with EtOAc The combined organic phases were washed with brine dried purified on flash column chromatography (isooctane/EtOAc/MeOH)

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

实验步骤: 5-bromo-2-(oxiran-2-ylmethoxy)phenyl formate (12.6 g, 46.0 mmol) was dissolved in dioxane (50 ml) and KOH (10%)/NaOH (20%) was added. Water and EtOAc was added and the phases were separated. The combined organic phases were washed with brine and dried to give the title compound (10.3 g). MS m/z (rel. intensity, 70 eV) 245 (M+, 96) 244 (M+, bp), 213 (29), 189 (46), 188 (49). the phases were separated The combined organic phases were washed with brine dried

反应条件: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a stirred solution of 5-bromosalicylaldehyde (5.0 g, 24.9 mmol), and epichlorohydrin (5.6 mL, 72.1 mmol) in 20 mL of DMF at 80° C. was added K2CO3 slowly in portions. The resulting mixture was then heated at 90° C. for 3 hours. Reaction was then stopped, water was added, extracted with diethyl ether. The organic extracts were washed with water, brine, dried over Na2SO4, concentrated in vacuo. The residue was purified on a SiO2 flash column chromatography eluting with 15-30% EtOAc/hexanes to give 2.82 g (44%) of the title compound as a colorless oil. Reaction extracted with diethyl ether The organic extracts were washed with water, brine dried over Na2SO4 concentrated in vacuo The residue was purified on a SiO2 flash column chromatography eluting with 15-30% EtOAc/hexanes

反应条件: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a stirred solution of 5-bromosalicylaldehyde (5.0 g, 24.9 mmol), and epichlorohydrin (5.6 mL, 72.1 mmol) in 20 mL of DMF at 80° C. was added K2CO3 slowly in portions. The resulting mixture was then heated at 90° C. for 3 h. Reaction was then stopped, water was added, extracted with diethyl ether. The organic extracts were washed with water, brine, dried over Na2SO4, concentrated in vacuo. The residue was purified on a SiO2 flash column chromatography eluting with 15-30% EtOAc/hexanes to give 2.82 g (44%) of the title compound as colorless oil. Reaction extracted with diethyl ether The organic extracts were washed with water, brine dried over Na2SO4 concentrated in vacuo The residue was purified on a SiO2 flash column chromatography eluting with 15-30% EtOAc/hexanes