Methanol → Methyl 3-bromo-4-methylbenzoate

A solution of 3-bromo-4-methylbenzoic acid (20 g, 93.00 mmol, 1.00 equiv) and sulfuric acid (20 mL) in methanol (100 mL) was stiffed overnight at 80° C. The mixture was then concentrated under reduced pressure and the residue was diluted with 500 mL of ethyl acetate. The resulting mixture was washed with 3×200 mL of water, 1×200 mL of sodium bicarbonate (aq), followed by 1×200 mL of brine. The organic phase was dried over anhydrous sodium sulfate, concentrated under reduced pressure, and dried to yield 20 g (94%) of the title compound as a dark red oil.

1. concentrationThe mixture was then concentrated under reduced pressure
2. additionthe residue was diluted with 500 mL of ethyl acetate
3. washThe resulting mixture was washed with 3×200 mL of water, 1×200 mL of sodium bicarbonate (aq)
4. dry with materialThe organic phase was dried over anhydrous sodium sulfate
5. concentrationconcentrated under reduced pressure
6. customdried

ORD record

ord-ba2ab83e631645ca9b4a0767cbc7d863

Source dataset

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08871790B2