2-amino-3-bromophenol

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

Procedure: BBr3 (3.71 mL, 3.71 mmol, 1 M in DCM) was added at 0° C. to a solution of 2-bromo-6-methoxyphenylamine (375 mg, 1.86 mmol) in DCM (10 mL). The reaction mixture was stirred under reflux for 2 hours and was quenched by the addition of MeOH followed by a saturated solution of NaHCO3. The aqueous phase was extracted with AcOEt. The resulting organic layer was washed with brine dried over MgSO4, filtered and evaporated. The crude residue was purified by flash chromatography (cyclohexane/AcOEt 7:3 to DCM) to yield 204 mg (1.08 mmol, 58%) of 2-amino-3-bromophenol as a solid. under reflux for 2 hours was quenched by the addition of MeOH The aqueous phase was extracted with AcOEt The resulting organic layer was washed with brine dried over MgSO4 filtered evaporated The crude residue was purified by flash chromatography (cyclohexane/AcOEt 7:3 to DCM)

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

Procedure: BBr3 (3.71 mL, 3.71 mmol, 1 M in DCM) was added at 0° C. to a solution of 2-bromo-6-methoxyphenylamine (375 mg, 1.86 mmol) in DCM (10 mL). The reaction mixture was stirred under reflux for 2 hours and was quenched by the addition of MeOH followed by a saturated solution of NaHCO3. The aqueous phase was extracted with AcOEt. The resulting organic layer was washed with brine dried over MgSO4, filtered and evaporated. The crude residue was purified by flash chromatography (cyclohexane/AcOEt 7:3 to DCM) to yield 204 mg (1.08 mmol, 58%) of 2-amino-3-bromophenol as a solid. under reflux for 2 hours was quenched by the addition of MeOH The aqueous phase was extracted with AcOEt The resulting organic layer was washed with brine dried over MgSO4 filtered evaporated The crude residue was purified by flash chromatography (cyclohexane/AcOEt 7:3 to DCM)

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

Procedure: BBr3 (3.71 mL, 3.71 mmol, 1 M in DCM) was added at 0° C. to a solution of 2-bromo-6-methoxyphenylamine (375 mg, 1.86 mmol) in DCM (10 mL). The reaction mixture was stirred under reflux for 2 hours and was quenched by the addition of MeOH followed by a saturated solution of NaHCO3. The aqueous phase was extracted with AcOEt. The resulting organic layer was washed with brine dried over MgSO4, filtered and evaporated. The crude residue was purified by flash chromatography (cyclohexane/AcOEt 7:3 to DCM) to yield 204 mg (1.08 mmol, 58%) of 2-amino-3-bromophenol as a solid. under reflux for 2 hours was quenched by the addition of MeOH The aqueous phase was extracted with AcOEt The resulting organic layer was washed with brine dried over MgSO4 filtered evaporated The crude residue was purified by flash chromatography (cyclohexane/AcOEt 7:3 to DCM)

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

Procedure: BBr3 (3.71 mL, 3.71 mmol, 1 M in DCM) was added at 0° C. to a solution of 2-bromo-6-methoxyphenylamine (375 mg, 1.86 mmol) in DCM (10 mL). The reaction mixture was stirred under reflux for 2 hours and was quenched by the addition of MeOH followed by a saturated solution of NaHCO3. The aqueous phase was extracted with AcOEt. The resulting organic layer was washed with brine dried over MgSO4, filtered and evaporated. The crude residue was purified by flash chromatography (cyclohexane/AcOEt 7:3 to DCM) to yield 204 mg (1.08 mmol, 58%) of 2-amino-3-bromophenol as a solid. under reflux for 2 hours was quenched by the addition of MeOH The aqueous phase was extracted with AcOEt The resulting organic layer was washed with brine dried over MgSO4 filtered evaporated The crude residue was purified by flash chromatography (cyclohexane/AcOEt 7:3 to DCM)

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

Procedure: BBr3 (3.71 mL, 3.71 mmol, 1 M in DCM) was added at 0° C. to a solution of 2-bromo-6-methoxyphenylamine (375 mg, 1.86 mmol) in DCM (10 mL). The reaction mixture was stirred under reflux for 2 hours and was quenched by the addition of MeOH followed by a saturated solution of NaHCO3. The aqueous phase was extracted with AcOEt. The resulting organic layer was washed with brine dried over MgSO4, filtered and evaporated. The crude residue was purified by flash chromatography (cyclohexane/AcOEt 7:3 to DCM) to yield 204 mg (1.08 mmol, 58%) of 2-amino-3-bromophenol as a solid. under reflux for 2 hours was quenched by the addition of MeOH The aqueous phase was extracted with AcOEt The resulting organic layer was washed with brine dried over MgSO4 filtered evaporated The crude residue was purified by flash chromatography (cyclohexane/AcOEt 7:3 to DCM)

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

Procedure: BBr3 (3.71 mL, 3.71 mmol, 1 M in DCM) was added at 0° C. to a solution of 2-bromo-6-methoxyphenylamine (375 mg, 1.86 mmol) in DCM (10 mL). The reaction mixture was stirred under reflux for 2 hours and was quenched by the addition of MeOH followed by a saturated solution of NaHCO3. The aqueous phase was extracted with AcOEt. The resulting organic layer was washed with brine dried over MgSO4, filtered and evaporated. The crude residue was purified by flash chromatography (cyclohexane/AcOEt 7:3 to DCM) to yield 204 mg (1.08 mmol, 58%) of 2-amino-3-bromophenol as a solid. under reflux for 2 hours was quenched by the addition of MeOH The aqueous phase was extracted with AcOEt The resulting organic layer was washed with brine dried over MgSO4 filtered evaporated The crude residue was purified by flash chromatography (cyclohexane/AcOEt 7:3 to DCM)

Conditions: temp:120.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 2-amino-3-bromophenol (480 mg, 2.6 mmol), polyphosphoric ester (PPE, 3.4 g) and trifluoroacetic acid (0.88 mL, 11.5 mmol) was heated to 100° C. under a nitrogen atmosphere overnight. A reflux condenser was added as was fresh PPE and the reaction heated to 120° C. for 8 hr. The reaction was cooled and diluted with methylene chloride. The solvent was removed by rotoevaporation. The residue was dissolved in fresh methylene chloride and successively washed with 2N sodium hydroxide solution and saturated salt solution. After drying over anhydrous magnesium sulfate and filtering, the solvent was removed by rotoevaporation. The residue was purified by flash column chromatography in silica gel eluted with 15% acetone in hexanes to yield the title compound (110 mg, 16% yield). A reflux condenser was added The reaction was cooled The solvent was removed by rotoevaporation The residue was dissolved in fresh methylene chloride successively washed with 2N sodium hydroxide solution and saturated salt solution After drying over anhydrous magnesium sulfate filtering the solvent was removed by rotoevaporation The residue was purified by flash column chromatography in silica gel eluted with 15% acetone in hexanes

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Following a literature procedure (Org. Prep. & Proc. Int. 22(5), 613 (1990)), a solution of 2-amino-3-bromophenol (800 mg, 4.25 mmol) and trimethylformate (0.685 mL, 6.25 mmol) in methanol (1.25 mL) was treated with concentrated hydrochloric acid (0.01 mL). The flask was fitted with a short path distillation apparatus. The temperature of the solution was slowly raised to 90° C. and maintained until the methanol had finished distilling. Upon cooling, the residue crystallized and was dissolved in diethyl ether (70 mL). This solution was successively washed with 5% sodium hydroxide solution and water and dried over anhydrous magnesium sulfate. After filtering, the solvents were removed by rotoevaporation and the residue was purified by flash column chromatography on silica gel eluted with 20% ethyl acetate in hexanes to yield the title compound (550 mg, 65% yield). The flask was fitted with a short path distillation apparatus had finished distilling Upon cooling the residue crystallized was dissolved in diethyl ether (70 mL) This solution was successively washed with 5% sodium hydroxide solution and water dried over anhydrous magnesium sulfate After filtering the solvents were removed by rotoevaporation the residue was purified by flash column chromatography on silica gel eluted with 20% ethyl acetate in hexanes

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

Procedure: To an ice cooled solution of 6-bromo-2-anisidine (1.01 g, 5 mmol) in methylene chloride (30 mL) was slowly added a 1.0 M solution of boron tribromide in methylene chloride (10 mL, 10 mmol) via syringe. The reaction was slowly warmed to room temperature and stirred overnight. Methanol (10 mL) was added and the solvents removed by rotoevaporation to give the title compound (0.87 g, 92% yield). the solvents removed by rotoevaporation

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

Procedure: BBr3 (3.71 mL, 3.71 mmol, 1 M in DCM) was added at 0° C. to a solution of 2-bromo-6-methoxyphenylamine (375 mg, 1.86 mmol) in DCM (10 mL). The reaction mixture was stirred under reflux for 2 hours and was quenched by the addition of MeOH followed by a saturated solution of NaHCO3. The aqueous phase was extracted with AcOEt. The resulting organic layer was washed with brine dried over MgSO4, filtered and evaporated. The crude residue was purified by flash chromatography (cyclohexane/AcOEt 7:3 to DCM) to yield 204 mg (1.08 mmol, 58%) of 2-amino-3-bromophenol as a solid. under reflux for 2 hours was quenched by the addition of MeOH The aqueous phase was extracted with AcOEt The resulting organic layer was washed with brine dried over MgSO4 filtered evaporated The crude residue was purified by flash chromatography (cyclohexane/AcOEt 7:3 to DCM)

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

Procedure: BBr3 (3.71 mL, 3.71 mmol, 1 M in DCM) was added at 0° C. to a solution of 2-bromo-6-methoxyphenylamine (375 mg, 1.86 mmol) in DCM (10 mL). The reaction mixture was stirred under reflux for 2 hours and was quenched by the addition of MeOH followed by a saturated solution of NaHCO3. The aqueous phase was extracted with AcOEt. The resulting organic layer was washed with brine dried over MgSO4, filtered and evaporated. The crude residue was purified by flash chromatography (cyclohexane/AcOEt 7:3 to DCM) to yield 204 mg (1.08 mmol, 58%) of 2-amino-3-bromophenol as a solid. under reflux for 2 hours was quenched by the addition of MeOH The aqueous phase was extracted with AcOEt The resulting organic layer was washed with brine dried over MgSO4 filtered evaporated The crude residue was purified by flash chromatography (cyclohexane/AcOEt 7:3 to DCM)

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

Procedure: BBr3 (3.71 mL, 3.71 mmol, 1 M in DCM) was added at 0° C. to a solution of 2-bromo-6-methoxyphenylamine (375 mg, 1.86 mmol) in DCM (10 mL). The reaction mixture was stirred under reflux for 2 hours and was quenched by the addition of MeOH followed by a saturated solution of NaHCO3. The aqueous phase was extracted with AcOEt. The resulting organic layer was washed with brine dried over MgSO4, filtered and evaporated. The crude residue was purified by flash chromatography (cyclohexane/AcOEt 7:3 to DCM) to yield 204 mg (1.08 mmol, 58%) of 2-amino-3-bromophenol as a solid. under reflux for 2 hours was quenched by the addition of MeOH The aqueous phase was extracted with AcOEt The resulting organic layer was washed with brine dried over MgSO4 filtered evaporated The crude residue was purified by flash chromatography (cyclohexane/AcOEt 7:3 to DCM)