2-(4-bromoanilino)-1-phenylethanol

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

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution containing 2-(4-bromoanilino)-1-phenyl-1-ethanol (0.74 g, 0.00253 mol), N,N-diisopropylethylamine (1.01 g, 0.00786 mol) and N,N-dimethylaminopyridine (0.092 g, 0.00076 mol) in anhydrous dichloromethane (32 mL) was cooled to 0° C. and a solution of triphosgene (0.38 g, 0.00127 mol) in anhydrous dichloromethane (8 mL) was added dropwise. The reaction mixture was slowly warmed up to ambient temperature while stirring under an atmosphere of nitrogen for eighteen hours. The organic phase was washed with a saturated solution of sodium bicarbonate in water (40 mL), brine (30 mL) and dried with magnesium sulfate. The solvent was removed under reduced pressure and the residue purified by flash chromatography on silica using ethyl acetate/n-heptane (1:5) as mobile phase to yield 3-(4-bromophenyl)-5-phenyl-1,3-oxazolan-2-one (0.62 g, 0.00192 mol) as a white solid. The reaction mixture was slowly warmed up to ambient temperature The organic phase was washed with a saturated solution of sodium bicarbonate in water (40 mL), brine (30 mL) dried with magnesium sulfate The solvent was removed under reduced pressure the residue purified by flash chromatography on silica

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

Procedure: A solution of 2-(4-bromoanilino)-1-phenyl-1-ethanone (3.50 g, 0.0121 mol) in anhydrous methanol (200 mL) was cooled to 0° C. and sodium borohydride (2.28 g, 0.0603 mol) was added at once. The mixture was allowed to warm up to ambient temperature while stirring under an atmosphere of nitrogen for three hours. The reaction was quenched by dropwise addition of acetic acid, the reaction mixture was concentrated under reduced pressure and the residue was partitioned between dichloromethane (120 mL) and water (85 mL). The organic phase was dried with magnesium sulfate and concentrated under reduced pressure to yield 2-(4-bromoanilino)-1-phenyl-1-ethanol (3.49 g, 0.0117 mol) as a yellow oil. The reaction was quenched by dropwise addition of acetic acid the reaction mixture was concentrated under reduced pressure the residue was partitioned between dichloromethane (120 mL) and water (85 mL) The organic phase was dried with magnesium sulfate concentrated under reduced pressure

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

Procedure: A solution of 2-(4-bromoanilino)-1-phenyl-1-ethanone (3.50 g, 0.0121 mol) in anhydrous methanol (200 mL) was cooled to 0° C. and sodium borohydride (2.28 g, 0.0603 mol) was added at once. The mixture was allowed to warm up to ambient temperature while stirring under an atmosphere of nitrogen for three hours. The reaction was quenched by dropwise addition of acetic acid, the reaction mixture was concentrated under reduced pressure and the residue was partitioned between dichloromethane (120 mL) and water (85 mL). The organic phase was dried with magnesium sulfate and concentrated under reduced pressure to yield 2-(4-bromoanilino)-1-phenyl-1-ethanol (3.49 g, 0.0117 mol) as a yellow oil. The reaction was quenched by dropwise addition of acetic acid the reaction mixture was concentrated under reduced pressure the residue was partitioned between dichloromethane (120 mL) and water (85 mL) The organic phase was dried with magnesium sulfate concentrated under reduced pressure

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution containing 2-(4-bromoanilino)-1-phenyl-1-ethanol (0.74 g, 0.00253 mol), N,N-diisopropylethylamine (1.01 g, 0.00786 mol) and N,N-dimethylaminopyridine (0.092 g, 0.00076 mol) in anhydrous dichloromethane (32 mL) was cooled to 0° C. and a solution of triphosgene (0.38 g, 0.00127 mol) in anhydrous dichloromethane (8 mL) was added dropwise. The reaction mixture was slowly warmed up to ambient temperature while stirring under an atmosphere of nitrogen for eighteen hours. The organic phase was washed with a saturated solution of sodium bicarbonate in water (40 mL), brine (30 mL) and dried with magnesium sulfate. The solvent was removed under reduced pressure and the residue purified by flash chromatography on silica using ethyl acetate/n-heptane (1:5) as mobile phase to yield 3-(4-bromophenyl)-5-phenyl-1,3-oxazolan-2-one (0.62 g, 0.00192 mol) as a white solid. The reaction mixture was slowly warmed up to ambient temperature The organic phase was washed with a saturated solution of sodium bicarbonate in water (40 mL), brine (30 mL) dried with magnesium sulfate The solvent was removed under reduced pressure the residue purified by flash chromatography on silica

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

Procedure: A solution of 2-(4-bromoanilino)-1-phenyl-1-ethanone (3.50 g, 0.0121 mol) in anhydrous methanol (200 mL) was cooled to 0° C. and sodium borohydride (2.28 g, 0.0603 mol) was added at once. The mixture was allowed to warm up to ambient temperature while stirring under an atmosphere of nitrogen for three hours. The reaction was quenched by dropwise addition of acetic acid, the reaction mixture was concentrated under reduced pressure and the residue was partitioned between dichloromethane (120 mL) and water (85 mL). The organic phase was dried with magnesium sulfate and concentrated under reduced pressure to yield 2-(4-bromoanilino)-1-phenyl-1-ethanol (3.49 g, 0.0117 mol) as a yellow oil. The reaction was quenched by dropwise addition of acetic acid the reaction mixture was concentrated under reduced pressure the residue was partitioned between dichloromethane (120 mL) and water (85 mL) The organic phase was dried with magnesium sulfate concentrated under reduced pressure

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

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution containing 2-(4-bromoanilino)-1-phenyl-1-ethanol (0.74 g, 0.00253 mol), N,N-diisopropylethylamine (1.01 g, 0.00786 mol) and N,N-dimethylaminopyridine (0.092 g, 0.00076 mol) in anhydrous dichloromethane (32 mL) was cooled to 0° C. and a solution of triphosgene (0.38 g, 0.00127 mol) in anhydrous dichloromethane (8 mL) was added dropwise. The reaction mixture was slowly warmed up to ambient temperature while stirring under an atmosphere of nitrogen for eighteen hours. The organic phase was washed with a saturated solution of sodium bicarbonate in water (40 mL), brine (30 mL) and dried with magnesium sulfate. The solvent was removed under reduced pressure and the residue purified by flash chromatography on silica using ethyl acetate/n-heptane (1:5) as mobile phase to yield 3-(4-bromophenyl)-5-phenyl-1,3-oxazolan-2-one (0.62 g, 0.00192 mol) as a white solid. The reaction mixture was slowly warmed up to ambient temperature The organic phase was washed with a saturated solution of sodium bicarbonate in water (40 mL), brine (30 mL) dried with magnesium sulfate The solvent was removed under reduced pressure the residue purified by flash chromatography on silica

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

Procedure: A solution of 2-(4-bromoanilino)-1-phenyl-1-ethanone (3.50 g, 0.0121 mol) in anhydrous methanol (200 mL) was cooled to 0° C. and sodium borohydride (2.28 g, 0.0603 mol) was added at once. The mixture was allowed to warm up to ambient temperature while stirring under an atmosphere of nitrogen for three hours. The reaction was quenched by dropwise addition of acetic acid, the reaction mixture was concentrated under reduced pressure and the residue was partitioned between dichloromethane (120 mL) and water (85 mL). The organic phase was dried with magnesium sulfate and concentrated under reduced pressure to yield 2-(4-bromoanilino)-1-phenyl-1-ethanol (3.49 g, 0.0117 mol) as a yellow oil. The reaction was quenched by dropwise addition of acetic acid the reaction mixture was concentrated under reduced pressure the residue was partitioned between dichloromethane (120 mL) and water (85 mL) The organic phase was dried with magnesium sulfate concentrated under reduced pressure

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution containing 2-(4-bromoanilino)-1-phenyl-1-ethanol (0.74 g, 0.00253 mol), N,N-diisopropylethylamine (1.01 g, 0.00786 mol) and N,N-dimethylaminopyridine (0.092 g, 0.00076 mol) in anhydrous dichloromethane (32 mL) was cooled to 0° C. and a solution of triphosgene (0.38 g, 0.00127 mol) in anhydrous dichloromethane (8 mL) was added dropwise. The reaction mixture was slowly warmed up to ambient temperature while stirring under an atmosphere of nitrogen for eighteen hours. The organic phase was washed with a saturated solution of sodium bicarbonate in water (40 mL), brine (30 mL) and dried with magnesium sulfate. The solvent was removed under reduced pressure and the residue purified by flash chromatography on silica using ethyl acetate/n-heptane (1:5) as mobile phase to yield 3-(4-bromophenyl)-5-phenyl-1,3-oxazolan-2-one (0.62 g, 0.00192 mol) as a white solid. The reaction mixture was slowly warmed up to ambient temperature The organic phase was washed with a saturated solution of sodium bicarbonate in water (40 mL), brine (30 mL) dried with magnesium sulfate The solvent was removed under reduced pressure the residue purified by flash chromatography on silica

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

Procedure: A solution of 2-(4-bromoanilino)-1-phenyl-1-ethanone (3.50 g, 0.0121 mol) in anhydrous methanol (200 mL) was cooled to 0° C. and sodium borohydride (2.28 g, 0.0603 mol) was added at once. The mixture was allowed to warm up to ambient temperature while stirring under an atmosphere of nitrogen for three hours. The reaction was quenched by dropwise addition of acetic acid, the reaction mixture was concentrated under reduced pressure and the residue was partitioned between dichloromethane (120 mL) and water (85 mL). The organic phase was dried with magnesium sulfate and concentrated under reduced pressure to yield 2-(4-bromoanilino)-1-phenyl-1-ethanol (3.49 g, 0.0117 mol) as a yellow oil. The reaction was quenched by dropwise addition of acetic acid the reaction mixture was concentrated under reduced pressure the residue was partitioned between dichloromethane (120 mL) and water (85 mL) The organic phase was dried with magnesium sulfate concentrated under reduced pressure