Acetonitrile → 3-(3-Bromophenyl)-3-oxopropanenitrile

n-Butyllithium (214 ml, 340 mmol, 1.6 M solution in hexane) was added dropwise to a solution of acetonitrile (23.8 ml, 460 mmol) in dry tetrahydrofuran (1000 ml) at −78° C. After stirring the reaction mixture for 20 min., a solution of 4-bromobenzoyl chloride in dry tetrahydrofuran (50 ml) was added dropwise over 20 min. After 1 h, saturated ammonium chloride was added (200 ml) and the reaction mixture was allowed to warm to room temperature. The product was extracted into ether and washed with 1N hydrochloric acid (400 ml). The organics were removed in vacuo and the residue was redissolved in ethyl acetate. Ammonium hydroxide was added to give a solid which was filtered, redissolved in ethyl acetate and washed with 2 N hydrochloric acid. The organic layer was washed with brine, dried over sodium sulfate and concentrated in vacuo to give 2-(3-bromobenzoyl)acetonitrile (16.6 g) as a solid.

1. waitAfter 1 h
2. extractionThe product was extracted into ether
3. washwashed with 1N hydrochloric acid (400 ml)
4. customThe organics were removed in vacuo
5. dissolutionthe residue was redissolved in ethyl acetate
6. additionAmmonium hydroxide was added
7. customto give a solid which
8. filtrationwas filtered
9. dissolutionredissolved in ethyl acetate
10. washwashed with 2 N hydrochloric acid
11. washThe organic layer was washed with brine
12. dry with materialdried over sodium sulfate
13. concentrationconcentrated in vacuo

ORD record

ord-add45351a0e54987ae75c0fc4cf911b9

Source dataset

uspto-grants-2005_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06979693B2