Boron tribromide → 2-Amino-5-bromo-3-fluorophenol

HRID 1487678Notes

Reaction equation

HRID 1487678 reaction equation
Br.[Br:2][C:3]1[CH:9]=[C:8]([O:10]C)[C:6]([NH2:7])=[C:5]([F:12])[CH:4]=1.B(Br)(Br)Br>C(Cl)Cl>[NH2:7][C:6]1[C:5]([F:12])=[CH:4][C:3]([Br:2])=[CH:9][C:8]=1[OH:10]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 867265044-Bromo-2-fluoro-6-methoxyaniline hydrobromide

Product 1

HCID 857118462-Amino-5-bromo-3-fluorophenolYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 4-bromo-2-fluoro-6-methoxyaniline hydrobromide (1 equiv) in DCM (0.3 M) was added boron tribromide (2 equiv) in DCM at 0° C. The reaction mixture was stirred at room temperature for 2 h. After quenching, the reaction mixture was diluted with DCM then purified by silica gel chromatography (0 to 100% ethyl acetate in hexane) to give the title compound (92% yield). MS (ESI) m/z 205.9 [M+H]+.

Workup

  1. customAfter quenching
  2. additionthe reaction mixture was diluted with DCM
  3. customthen purified by silica gel chromatography (0 to 100% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-ef4bed43ccc54dfaa6f6845533c4e442
Source dataset
uspto-grants-2016_08
Patent number
US09428509B2

Reaction notes

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