Methanol → 2-Amino-3-bromophenol

HRID 1596600Notes

Reaction equation

HRID 1596600 reaction equation
Br[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]([NH2:10])[C:7]=1[O:8]C.B(Br)(Br)[Br:12].CO>C(Cl)Cl>[NH2:10][C:6]1[C:5]([Br:12])=[CH:4][CH:3]=[CH:2][C:7]=1[OH:8]

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 226677353-Bromo-2-methoxyaniline

Product 1

HCID 217022522-Amino-3-bromophenolYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

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).

Workup

  1. customthe solvents removed by rotoevaporation

Sources & evidence

ORD record
ord-7ad3dc0913f244708ff88f203ba1fa02
Source dataset
uspto-grants-2001_09
Patent number
US06291511B1

Reaction notes

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