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ChemicalBook CAS DataBase List 3,5-DIFLUORO-4-HYDROXY-BENZONITRILE

3,5-DIFLUORO-4-HYDROXY-BENZONITRILE synthesis

5synthesis methods

Product Name:3,5-DIFLUORO-4-HYDROXY-BENZONITRILE
CAS Number:2967-54-6
Molecular formula:C7H3F2NO
Molecular Weight:155.1

104197-15-1
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2967-54-6
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Yield: 80.6%

Reaction Conditions:

Stage #1:3,5-difluoro-4-methoxybenzonitrile with boron tribromide in dichloromethane at -78 - 20;
Stage #2: with water in dichloromethane at 0;

Steps:

B.iv
(iv) 3,5-Difluoro-4-hydroxybenzonitrileBBr₃ (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 -78⁰C. 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.

References:

ASTRAZENECA AB WO2006/135316, 2006, A1 Location in patent:Page/Page column 55