Boron tribromide → 2-Amino-3-bromophenol

HRID 422314Notes

Reaction equation

HRID 422314 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-25fd994a600941cb820aa4c89a4197d8
Source dataset
uspto-grants-2012_01
Patent number
US08101637B2

Reaction notes

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