Dimethylformamide → 4-Formyl-2-methylbenzoic acid

Temperature

-78 °C

To a stirred solution of 4-bromo-2-methylbenzoic acid (10 g, 46.4 mmol) in dry THF (360 mL) at −78° C. was added n-butyllithium (n-BuLi, 1.6 M solution in hexane; 58.17 mL, 93.0 mmol) and DMF (8 mL). The reaction mixture was stirred at −78° C. for 1 h then was warmed to 25° C. and stirred for 1 h. The reaction mixture was quenched with 1 N HCl solution and extracted with EtOAc. The combined EtOAc extracts were washed with brine and dried over Na2SO4 and concentrated under reduced pressure. The residue was washed with n-hexane to afford the title compound as a solid (3.0 g, 40%): mp 196-198° C.; 1H NMR (400 MHz, DMSO-d6) δ 13.32 (br s, 1H), 10.05 (s, 1H), 7.98 (m, 1H), 7.84 (m, 2H), 2.61 (s, 3H); ESIMS m/z 163.00 ([M−H]−).

1. temperaturethen was warmed to 25° C.
2. stirringstirred for 1 h
3. customThe reaction mixture was quenched with 1 N HCl solution
4. extractionextracted with EtOAc
5. washThe combined EtOAc extracts were washed with brine
6. dry with materialdried over Na2SO4
7. concentrationconcentrated under reduced pressure
8. washThe residue was washed with n-hexane

ORD record

ord-3cbdb909d42145d7a1b6c9e10b14836a

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09212163B2