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) δ 3.10 (s, 2H), 3.82 (s, 2H), 7.20-7.29 (m, 2H), 7.39-7.42 (dd, 1H), 7.52 (dr 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-3851a83a1fec49549fedf1b4ff686d2f

Source dataset

uspto-grants-1997_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05639759