4-Fluorobenzenesulfonyl chloride → Sodium 4-fluorobenzene sulfinate

Temperature

0 °C

A solution of 4-fluorobenzenesulfonyl chloride (2 g, 10.28 mmol) in 50 mL of THF (distilled from Na-benzophenone) is cooled to 0+ C. and sodium borohydride (1.9 g, 51.4 mmol) is added portionwise. The reaction is stirred at 0° C. for 2 h, then warmed to RT, and after 2 h, quenched with water (5 mL). The solvent is evaporated and the aqueous residue is acidified by addition of aqueous 6N HCl. The product is taken up in EtOAc, washed with brine, dried over anhydrous Na2SO4 and concentrated to give 4-fluorobenzenesulfinic acid: NMR (DMSO-d6) 7.12 (app t, 2H, J=8.3), 7.5 (dd, 2H, J=8.3, 6); ESI-MS 159 [M−1]−.

1. temperaturewarmed to RT
2. waitafter 2 h
3. customquenched with water (5 mL)
4. customThe solvent is evaporated
5. additionthe aqueous residue is acidified by addition of aqueous 6N HCl
6. washwashed with brine
7. dry with materialdried over anhydrous Na2SO4
8. concentrationconcentrated

ORD record

ord-10c8b18a6e594cc2b39cf46c301c8b7e

Source dataset

uspto-grants-2003_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06599942B1