4-Bromobenzoic acid → 4-Bromo-3-(chlorosulfonyl)benzoic acid

Temperature

130 °C

4-Bromobenzoic acid (10 g, 49.75 mmol) was added portion wise to chlorosulfonic acid (25 ml, 373.13 mmol) at 0° C. The mixture was heated to 130° C. for 10 hours, until complete consumption of the starting material was observed by LCMS. The reaction mixture was allowed to cool down to ambient temperature, then added drop wise to an ice/water mixture (500 ml). The precipitate was filtered and washed with cold water (2×100 ml). The solid recovered was dissolved in diethyl ether, the solution then dried over sodium sulphate, filtered and concentrated in vacuo to afford the expected product as a beige solid (11.85 g, 79% yield); δH (400 MHz, DMSO) 8.45 (1H, d, 1.7 Hz), 7.72 (1H, d, 2.2 Hz), 7.71 (1H, s); TR=2.08 min.

1. temperatureto cool down to ambient temperature
2. filtrationThe precipitate was filtered
3. washwashed with cold water (2×100 ml)
4. customThe solid recovered
5. dissolutionwas dissolved in diethyl ether
6. dry with materialthe solution then dried over sodium sulphate
7. filtrationfiltered
8. concentrationconcentrated in vacuo

ORD record

ord-51b6ca691b2943d696bbbe530ea93568

Source dataset

uspto-grants-2012_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08227639B2