Thioglycolic Acid → HCID 178526169, compound

To a solution of 3-bromobenzyl bromide (23.75 g, 90 mmol) and thioglycolic acid (11.42 g, 120 mmol) in ethanol (150 mL) was added potassium hydroxide (14.24 g, 250 mmol) in water (50 mL). The reaction was heated at reflux for 3.5 h, cooled and the ethanol was evaporated. The residue was quenched with water (100 mL) and the mixture was extracted with ether (50 mL). The aqueous layer was acidified to pH 1 with concentrated hydrochloric acid, extracted with ethyl acetate (2×100 mL) and the organic phase was dried. Evaporation of the solvent followed by washing of the residue with hexane afforded 3-bromophenylmethylthioacetic acid as a white solid (92%), mp 90°-91° C.: 1H NMR (CDCl3) δ3.10 (s, 2H), 3.82 (s, 2H), 7.20-7.29 (m, 2H), 7.39-7.42 (dd, 1H), 7.52 (d, 1H); IR (KBr) 1706 cm-1 ; Mass spectrum m/z 280 (M+NH4); Anal. calcd. for C9H9O2SBr: C 41.39, H 3.47, S 12.28; Found C 41.43, H 3.49, S 12.10.

1. temperatureThe reaction was heated
2. temperatureat reflux for 3.5 h
3. temperaturecooled
4. customthe ethanol was evaporated
5. customThe residue was quenched with water (100 mL)
6. extractionthe mixture was extracted with ether (50 mL)
7. extractionextracted with ethyl acetate (2×100 mL)
8. customthe organic phase was dried
9. customEvaporation of the solvent
10. washby washing of the residue with hexane

ORD record

ord-cd69c48598cb494798ccebfd7e04088b

Source dataset

uspto-grants-1995_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05428040