Boron tribromide → 2-Amino-5-bromo-4-chlorophenol

HRID 1036077Notes

Reaction equation

HRID 1036077 reaction equation
[Br:1][C:2]1[CH:8]=[C:7]([O:9]C)[C:5]([NH2:6])=[CH:4][C:3]=1[Cl:11].B(Br)(Br)Br>C(Cl)Cl>[NH2:6][C:5]1[CH:4]=[C:3]([Cl:11])[C:2]([Br:1])=[CH:8][C:7]=1[OH:9]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 229976674-Bromo-5-chloro-2-methoxyaniline

Product 1

HCID 584871002-Amino-5-bromo-4-chlorophenolYield 97.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 4-bromo-3-chloro-6-methoxyaniline (28) (944 mg, 4 mmol) in 10 ml DCM was added 1 M BBr3 in DCM (8 ml, 8 mmol). The reaction mixture was stirred at r.t. for 2 h, which turned to a brown solution and back to a brown suspension. After quenched with aq. sodium bicarbonate solution, the mixture was extracted with EA. The org. phase was washed with brine, dried over sodium sulfate, concentrated to dryness to give 865 mg of 29 as a brown solid. Yield: 97.2%, purity>95%.

Workup

  1. customAfter quenched with aq. sodium bicarbonate solution
  2. extractionthe mixture was extracted with EA
  3. washphase was washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-d3ff9ed3cc7a414b8f5f0b91e5459e6e
Source dataset
uspto-grants-2013_10
Patent number
US08546403B2

Reaction notes

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