Boron tribromide → 3,5-Difluoro-4-hydroxy-benzonitrile

HRID 2078404Notes

Reaction equation

HRID 2078404 reaction equation
B(Br)(Br)Br.[F:5][C:6]1[CH:7]=[C:8]([CH:11]=[C:12]([F:16])[C:13]=1[O:14]C)[C:9]#[N:10]>ClCCl>[F:5][C:6]1[CH:7]=[C:8]([CH:11]=[C:12]([F:16])[C:13]=1[OH:14])[C:9]#[N:10]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 105832533,5-Difluoro-4-methoxybenzonitrile

Product 1

HCID 107494063,5-Difluoro-4-hydroxy-benzonitrileYield 80.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

BBr3 (6.61 g, 0.0264 mol) was added to 3,5-difluoro-4-methoxybenzonitrile (1.5 g, 0.0088 mol; see step (iii) above) in dichloromethane (15 mL) at −78° C. Stirring was continued at room temperature overnight under a nitrogen atmosphere. The reaction mixture was then quenched with ice water and extracted with dichloromethane. The organic layer was washed with water and brine, and dried over sodium sulfate. Solvent evaporation under reduced pressure yielded 1.1 g (80.6%) of the sub-title compound as a grey solid.

Workup

  1. customThe reaction mixture was then quenched with ice water
  2. extractionextracted with dichloromethane
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. customSolvent evaporation under reduced pressure

Sources & evidence

ORD record
ord-38dba6673d774ba980e32dd270ce18ad
Source dataset
uspto-grants-2011_04
Patent number
US07928225B2

Reaction notes

Loading…