Boron Trichloride → 4-Amino-2-bromophenol

HRID 1157156Notes

Reaction equation

HRID 1157156 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([O:8]CC2C=CC=CC=2)=[C:4]([Br:16])[CH:3]=1.B(Cl)(Cl)Cl>ClCCl>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([Br:16])[CH:3]=1

Participants

4

Reactant 2

HCID 25135Boron TrichlorideHCID 220177374-Benzyloxy-3-bromophenylamine

Product 1

HCID 144402654-Amino-2-bromophenolYield 56%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-amino-1-benzyloxy-2-bromobenzene in 2 mL of dichloromethane at −78 C was added boron trichloride (0.4 mL, 1 M in DCM) dropwise. The reaction was quenched with water at 0 C, concentrated and dried under vacuum to afford 4-amino-2-bromo-1-hydroxybenzene (17 mg, 56% two steps)

Workup

  1. customThe reaction was quenched with water at 0 C
  2. concentrationconcentrated
  3. customdried under vacuum

Sources & evidence

ORD record
ord-3ae0cd9993264b1a84990d5f8de9d37e
Source dataset
uspto-grants-2010_10
Patent number
US07807672B2

Reaction notes

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