Carbon Dioxide → 4-Cyano-2-methylbenzoic acid

Temperature

-78 °C

To a solution of 4-bromo-3-methyl-benzonitrile (10.008 g, 51.05 mmol) (commercially available) in tetrahydrofuran (“THF”) (350 ml) was added n-butyl lithium (1.6M in THF) (35 ml, 56.16 mmol) at −78° C. The reaction mixture was stirred at −78° C. for 1 hour. Then carbon dioxide (24.933 g, 566.66 mmol) was added. The reaction mixture was allowed to warm to ambient temperature. The reaction mixture was quenched by addition of water (300 ml), and extracted with diethyl ether (3×300 ml). The phases were separated. The aqueous phase was acidified by addition of aqueous hydrochloric acid (concentrated) and extracted with chloroform (3×200 ml). The combined organic phases were concentrated and used without further purification.

1. temperatureto warm to ambient temperature
2. customThe reaction mixture was quenched by addition of water (300 ml)
3. extractionextracted with diethyl ether (3×300 ml)
4. customThe phases were separated
5. additionThe aqueous phase was acidified by addition of aqueous hydrochloric acid (concentrated)
6. extractionextracted with chloroform (3×200 ml)
7. concentrationThe combined organic phases were concentrated
8. customused without further purification

ORD record

ord-f154574c77d24f489cdc6e29f8004c34

Source dataset

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08658698B2