Dimethylformamide → 4-Bromo-3-(hydroxymethyl)benzonitrile

A mixture of 2 (20.0 mmol), (methoxymethyl)triphenylphosphonium chloride (8.49 g, 24.0 mmol), and potassium tert-butoxide (2.83 g, 24.0 mol) in N,N-dimethylformamide (50 mL) was stirred at room temperature for overnight. The reaction was quenched with 6 N HCl, and the mixture was extracted with ethyl acetate. The organic layer was washed with water (×2) and brine, and dried on anhydrous sodium sulfate. The solvent was removed under reduced. To the residue were added tetrahydrofuran (60 mL) and 6 N HCl, and the mixture was heated at reflux for 8 h. Water was added, and the mixture was extracted with ether. The organic layer was washed with brine and dried on anhydrous sodium sulfate. The solvent was removed under reduced pressure to afford 16.6 mmol of 9.

1. customThe reaction was quenched with 6 N HCl
2. extractionthe mixture was extracted with ethyl acetate
3. washThe organic layer was washed with water (×2) and brine
4. dry with materialdried on anhydrous sodium sulfate
5. customThe solvent was removed
6. additionTo the residue were added tetrahydrofuran (60 mL) and 6 N HCl
7. temperaturethe mixture was heated
8. temperatureat reflux for 8 h
9. additionWater was added
10. extractionthe mixture was extracted with ether
11. washThe organic layer was washed with brine
12. dry with materialdried on anhydrous sodium sulfate
13. customThe solvent was removed under reduced pressure

ORD record

ord-c603e60534e44b48a386a5796672f399

Source dataset

uspto-grants-2011_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08039451B2