Boron tribromide → 3-Fluoro-4-hydroxybenzonitrile

HRID 1992364Notes

Reaction equation

HRID 1992364 reaction equation
B(Br)(Br)Br.[F:5][C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][C:13]=1[O:14]C)[C:9]#[N:10]>ClCCl>[F:5][C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][C:13]=1[OH:14])[C:9]#[N:10]

Participants

4

Reactant 2

HCID 25134Boron tribromide2×HCID 27745483-Fluoro-4-methoxybenzonitrile

Product 1

HCID 27829443-Fluoro-4-hydroxybenzonitrileYield 91.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

BBr3 (23 ml, 0.242 mol) was added to 3-Fluoro-4-methoxy-benzonitrile (24.4 g, 0.16 mol) in dichloromethane (200 ml) at −78° C. and stirring continued overnight at room temperature. Another portion of BBr3 (23 ml, 0.242 mol) was added at −78° C. and stirring continued at RT for 2 days under nitrogen atmosphere. The reaction mixture was quenched with ice water and extracted with dichloromethane. Organic layer was washed with water and brine, and dried over sodium sulfate. Solvent evaporation under reduced pressure gave 20 g of the sub-title compound as a solid. This was taken for next step without further purification.

Workup

  1. stirringstirring
  2. waitcontinued at RT for 2 days under nitrogen atmosphere
  3. customThe reaction mixture was quenched with ice water
  4. extractionextracted with dichloromethane
  5. washOrganic layer was washed with water and brine
  6. dry with materialdried over sodium sulfate
  7. customSolvent evaporation under reduced pressure

Sources & evidence

ORD record
ord-a847697db3384dbca1e1300e8581bb9e
Source dataset
uspto-grants-2010_01
Patent number
US07648985B2

Reaction notes

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