Boron tribromide → 2-Amino-3-bromophenol

HRID 1189115Notes

Reaction equation

HRID 1189115 reaction equation
B(Br)(Br)Br.[Br:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12]C)[C:7]=1[NH2:14]>C(Cl)Cl>[NH2:14][C:7]1[C:6]([Br:5])=[CH:11][CH:10]=[CH:9][C:8]=1[OH:12]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 2322702-Bromo-6-methoxyaniline

Product 1

HCID 217022522-Amino-3-bromophenolYield 58.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

BBr3 (3.71 mL, 3.71 mmol, 1 M in DCM) was added at 0° C. to a solution of 2-bromo-6-methoxyphenylamine (375 mg, 1.86 mmol) in DCM (10 mL). The reaction mixture was stirred under reflux for 2 hours and was quenched by the addition of MeOH followed by a saturated solution of NaHCO3. The aqueous phase was extracted with AcOEt. The resulting organic layer was washed with brine dried over MgSO4, filtered and evaporated. The crude residue was purified by flash chromatography (cyclohexane/AcOEt 7:3 to DCM) to yield 204 mg (1.08 mmol, 58%) of 2-amino-3-bromophenol as a solid.

Workup

  1. temperatureunder reflux for 2 hours
  2. customwas quenched by the addition of MeOH
  3. extractionThe aqueous phase was extracted with AcOEt
  4. washThe resulting organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated
  8. customThe crude residue was purified by flash chromatography (cyclohexane/AcOEt 7:3 to DCM)

Sources & evidence

ORD record
ord-a2f9e3809dc349249dcbd62c6fdbe041
Source dataset
uspto-grants-2014_03
Patent number
US08674106B2

Reaction notes

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