Boron tribromide → 2-Amino-3-bromophenol

HRID 334587Notes

Reaction equation

HRID 334587 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-e367673db517437bb11b8cd2474bedf5
Source dataset
uspto-grants-2014_11
Patent number
US08883826B2

Reaction notes

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