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

HRID 530781Notes

Reaction equation

HRID 530781 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 101.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 4-bromo-3-chloro-6-methoxyaniline (52) (5 g, 21.1 mmol) in 50 ml DCM was added 1 M BBr3 in DCM (43 ml, 43 mmol) at 0° C. The reaction mixture was stirred at r.t. for 3 h, which turned to a light brown solution and back to a light 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 4.746 g 53 as light brown solid. Yield: 100%, 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-417b84f831ab4cca88b4f3931d1264e9
Source dataset
uspto-grants-2016_05
Patent number
US09353099B2

Reaction notes

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