Boron tribromide → 4-Bromo-3-nitrophenol

HRID 431389Notes

Reaction equation

HRID 431389 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8]C)=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].B(Br)(Br)Br>ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11]

Participants

4

Reactant 2

HCID 25134Boron tribromide2×HCID 792884-Bromo-3-nitroanisole

Product 1

HCID 158178674-Bromo-3-nitrophenolYield 68.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 1-bromo-4-methoxy-2-nitrobenzene (2.32 g, 10 mmol) in 75 mL of dichloromethane at 0° C. was added BBr3 solution (1 M in DCM, 12 mL, 12 mmol) dropwise. The solution was allowed to warm to room temperature and stirred for 16 h. GC/MS showed starting material still left so another 12 mL of BBr3 solution was added and the reaction mixture refluxed for 4 h. The reaction mixture was cooled in ice and quenched with water. After washing successively with saturated NaHCO3(aq) and brine, the organic layer was dried over MgSO4, filtered and evaporated. The resulting yellow solid was flash chromatographed (25% EtOAc/hexane) to give 1.5 g of product in (69%) yield as a pale yellow solid: MS (EI) m/z 218 (M+).

Workup

  1. additionwas added
  2. temperaturethe reaction mixture refluxed for 4 h
  3. temperatureThe reaction mixture was cooled in ice
  4. customquenched with water
  5. washAfter washing successively with saturated NaHCO3(aq) and brine
  6. dry with materialthe organic layer was dried over MgSO4
  7. filtrationfiltered
  8. customevaporated
  9. customchromatographed (25% EtOAc/hexane)

Sources & evidence

ORD record
ord-104232f3e11146ffb929231e07ad212a
Source dataset
uspto-grants-2003_12
Patent number
US06656971B2

Reaction notes

Loading…