Boron tribromide → 2-Bromo-5-nitrophenol

HRID 330787Notes

Reaction equation

HRID 330787 reaction equation
B(Br)(Br)Br.[Br:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][C:7]=1[O:15]C>C(Cl)Cl>[Br:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][C:7]=1[OH:15]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 1012932-Bromo-5-nitroanisole

Product 1

HCID 128671362-Bromo-5-nitrophenolYield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

BBr3 (8.58 mL of 1.0M solution, 8.6 mmol) was added to the DCM (10 mL) solution of 1-bromo-2-methoxy-4-nitrobenzene (1.0 g, 4.3 mmol) at 0° C. The reaction mixture was warmed to room temperature and stirred overnight. The mixture was quenched with water and extracted with ethyl acetate (3×20 mL). The combined extracts were dried and the crude was purified by flash column chromatography to get the desired compound as pale brown powder in 65% yield (600 mg).

Workup

  1. customThe mixture was quenched with water
  2. extractionextracted with ethyl acetate (3×20 mL)
  3. customThe combined extracts were dried
  4. customthe crude was purified by flash column chromatography

Sources & evidence

ORD record
ord-c78f0255ddd5448f8298883d429ea4a4
Source dataset
uspto-grants-2014_11
Patent number
US08877752B2

Reaction notes

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