Boron tribromide → 3-Fluoro-4-hydroxybenzonitrile

HRID 2078411Notes

Reaction equation

HRID 2078411 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; see step (iii) above) in dichloromethane (200 mL) at −78° C. Stirring was continued at room temperature overnight. Another portion of BBr3 (23 mL, 0.242 mol) was added at −78° C. and stirring was continued at RT for a further 2 days under a nitrogen atmosphere. The reaction mixture was quenched with ice water and extracted with dichloromethane. The organic layer was washed with water and brine, and then dried over sodium sulfate. Solvent evaporation under reduced pressure gave 20 g of the sub-title compound as a solid. This was employed directly in the next step without further purification.

Workup

  1. stirringstirring
  2. waitwas continued at RT for a further 2 days under a nitrogen atmosphere
  3. customThe reaction mixture was quenched with ice water
  4. extractionextracted with dichloromethane
  5. washThe organic 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-ee39dbb9b08d46cb9664ea7c39af4dfe
Source dataset
uspto-grants-2011_04
Patent number
US07928225B2

Reaction notes

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