Dimethylformamide → 3-Formyl-4-methylbenzoic acid

To a stirred solution of 3-bromo-4-methylbenzoic acid (2.14 g, 10.0 mmol) in tetrahydrofuran (30 mL) under nitrogen at -78° C. was added n-BuLi (10 mL, 2.5 M in THF, 25 mmol) drop-wise. The mixture was stirred for 1 h below −70° C., then DMF (5 mL) was slowly added. The resulting solution was slowly warmed to room temperature and stirred for 1 h, then carefully quenched by slow addition of water (50 mL). The pH was adjusted to −3-4 using aqueous HCl (6 M) and the resulting mixture was extracted with ethyl acetate (2×50 mL). The combined organics was dried (Na2SO4), filtered, and concentrated under reduced pressure to yield the title compound as a yellow solid (1.6 g, 98%).

1. stirringstirred for 1 h
2. customcarefully quenched by slow addition of water (50 mL)
3. extractionthe resulting mixture was extracted with ethyl acetate (2×50 mL)
4. dry with materialThe combined organics was dried (Na2SO4)
5. filtrationfiltered
6. concentrationconcentrated under reduced pressure

ORD record

ord-fec0a68721f64655bd79e91b92393716

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09428502B2