1-(5-bromo-3-fluoro-2-hydroxyphenyl)ethanone

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Preparation according to Preparation 1 using 1-(5-bromo-3-fluoro-2-hydroxyphenyl)ethanone (16.8 g, 72 mmol), (R)-glycidyltosylate (18.1 g, 79 mmol), K2CO3 (15.0 g, 108 mmol) and DMF (60 ml). The combined organic phases were washed with LiCl (5%), HCl (1 N). Flash column chromatography (isooctane/EtOAc) yielded the title compound (8.3 g). MS m/z (rel. intensity, 70 eV) 290 (M+, 9), 288 (M+, 9), 217 (bp), 81 (47), 57 (46). Preparation The combined organic phases were washed with LiCl (5%), HCl (1 N)

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 1-(5-bromo-3-fluoro-2-hydroxyphenyl)ethanone (3.7 g, 15.8 mmol), epibromohydrin (2.6 ml, 31.7 mmol) and K2CO3 (3.3 g, 23.8 mmol) in DMF (20 ml) was heated at 60° C. for 1 h 50 min. The solution was brought to ambient temperature and water and EtOAc was added. The water phase was extracted with EtOAc. The combined organic phases were washed with LiCl (5%), HCl (1 N) and brine and were dried (Na2SO4) and evaporated to dryness. Purification on flash column chromatography (isooctane/EtOAc) gave the title compound (3.9 g). MS m/z (rel. intensity, 70 eV) 289 (M+, 13), 288 (M+, 14), 218 (91), 217 (bp), 81 (39), 57 (95). was brought to ambient temperature The water phase was extracted with EtOAc The combined organic phases were washed with LiCl (5%), HCl (1 N) and brine were dried (Na2SO4) evaporated to dryness Purification on flash column chromatography (isooctane/EtOAc)

Conditions: temp:150.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: AlCl3 (5.0 g, 38 mmol) was added in portions to 4-bromo-2-fluorophenyl acetate (5.8 g, 25 mmol). The mixture was heated at 150° C. for 3 h and then brought to ambient temperature. Water (ice-cold) was slowly added and then EtOAc. The resulting mixture was vigorously stirred and then the phases were separated and the water phase extracted with EtOAc. The combined organic phases were washed with brine, dried (Na2SO4) and evaporated to dryness to give the title compound (5.3 g). MS m/z (rel. intensity, 70 eV) 233 (M+, 55), 232 (M+, 56), 218 (98), 217 (bp), 161 (10). brought to ambient temperature the phases were separated the water phase extracted with EtOAc The combined organic phases were washed with brine dried (Na2SO4) evaporated to dryness

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Preparation according to Preparation 1 using 1-(5-bromo-3-fluoro-2-hydroxyphenyl)ethanone (16.8 g, 72 mmol), (R)-glycidyltosylate (18.1 g, 79 mmol), K2CO3 (15.0 g, 108 mmol) and DMF (60 ml). The combined organic phases were washed with LiCl (5%), HCl (1 N). Flash column chromatography (isooctane/EtOAc) yielded the title compound (8.3 g). MS m/z (rel. intensity, 70 eV) 290 (M+, 9), 288 (M+, 9), 217 (bp), 81 (47), 57 (46). Preparation The combined organic phases were washed with LiCl (5%), HCl (1 N)

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 1-(5-bromo-3-fluoro-2-hydroxyphenyl)ethanone (3.7 g, 15.8 mmol), epibromohydrin (2.6 ml, 31.7 mmol) and K2CO3 (3.3 g, 23.8 mmol) in DMF (20 ml) was heated at 60° C. for 1 h 50 min. The solution was brought to ambient temperature and water and EtOAc was added. The water phase was extracted with EtOAc. The combined organic phases were washed with LiCl (5%), HCl (1 N) and brine and were dried (Na2SO4) and evaporated to dryness. Purification on flash column chromatography (isooctane/EtOAc) gave the title compound (3.9 g). MS m/z (rel. intensity, 70 eV) 289 (M+, 13), 288 (M+, 14), 218 (91), 217 (bp), 81 (39), 57 (95). was brought to ambient temperature The water phase was extracted with EtOAc The combined organic phases were washed with LiCl (5%), HCl (1 N) and brine were dried (Na2SO4) evaporated to dryness Purification on flash column chromatography (isooctane/EtOAc)

Conditions: temp:150.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: AlCl3 (5.0 g, 38 mmol) was added in portions to 4-bromo-2-fluorophenyl acetate (5.8 g, 25 mmol). The mixture was heated at 150° C. for 3 h and then brought to ambient temperature. Water (ice-cold) was slowly added and then EtOAc. The resulting mixture was vigorously stirred and then the phases were separated and the water phase extracted with EtOAc. The combined organic phases were washed with brine, dried (Na2SO4) and evaporated to dryness to give the title compound (5.3 g). MS m/z (rel. intensity, 70 eV) 233 (M+, 55), 232 (M+, 56), 218 (98), 217 (bp), 161 (10). brought to ambient temperature the phases were separated the water phase extracted with EtOAc The combined organic phases were washed with brine dried (Na2SO4) evaporated to dryness

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Preparation according to Preparation 1 using 1-(5-bromo-3-fluoro-2-hydroxyphenyl)ethanone (16.8 g, 72 mmol), (R)-glycidyltosylate (18.1 g, 79 mmol), K2CO3 (15.0 g, 108 mmol) and DMF (60 ml). The combined organic phases were washed with LiCl (5%), HCl (1 N). Flash column chromatography (isooctane/EtOAc) yielded the title compound (8.3 g). MS m/z (rel. intensity, 70 eV) 290 (M+, 9), 288 (M+, 9), 217 (bp), 81 (47), 57 (46). Preparation The combined organic phases were washed with LiCl (5%), HCl (1 N)

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 1-(5-bromo-3-fluoro-2-hydroxyphenyl)ethanone (3.7 g, 15.8 mmol), epibromohydrin (2.6 ml, 31.7 mmol) and K2CO3 (3.3 g, 23.8 mmol) in DMF (20 ml) was heated at 60° C. for 1 h 50 min. The solution was brought to ambient temperature and water and EtOAc was added. The water phase was extracted with EtOAc. The combined organic phases were washed with LiCl (5%), HCl (1 N) and brine and were dried (Na2SO4) and evaporated to dryness. Purification on flash column chromatography (isooctane/EtOAc) gave the title compound (3.9 g). MS m/z (rel. intensity, 70 eV) 289 (M+, 13), 288 (M+, 14), 218 (91), 217 (bp), 81 (39), 57 (95). was brought to ambient temperature The water phase was extracted with EtOAc The combined organic phases were washed with LiCl (5%), HCl (1 N) and brine were dried (Na2SO4) evaporated to dryness Purification on flash column chromatography (isooctane/EtOAc)

Conditions: temp:150.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: AlCl3 (5.0 g, 38 mmol) was added in portions to 4-bromo-2-fluorophenyl acetate (5.8 g, 25 mmol). The mixture was heated at 150° C. for 3 h and then brought to ambient temperature. Water (ice-cold) was slowly added and then EtOAc. The resulting mixture was vigorously stirred and then the phases were separated and the water phase extracted with EtOAc. The combined organic phases were washed with brine, dried (Na2SO4) and evaporated to dryness to give the title compound (5.3 g). MS m/z (rel. intensity, 70 eV) 233 (M+, 55), 232 (M+, 56), 218 (98), 217 (bp), 161 (10). brought to ambient temperature the phases were separated the water phase extracted with EtOAc The combined organic phases were washed with brine dried (Na2SO4) evaporated to dryness