Hydrogen Bromide → 2-(4-Chlorophenyl)ethane-1-thiol

A mixture of 4-chlorophenethyl alcohol (50.0 g, 0.319 mole), thiourea (24.3 g, 0.319 mole) and 48% hydrobromic acid (161 g, 0.958 mole) was stirred under reflux for 9 hours. The mixture was cooled and a solution of sodium hydroxide (38.3 g, 0.958 mole) in water (380 ml) added, and the resulting mixture was stirred at reflux for 2 hours under a gentle stream of nitrogen. The mixture was cooled and the oily organic layer separated. The aqueous layer was acidified with hydrochloric acid and extracted with 3×50 ml portions of diethyl ether. The ethereal extracts were combined with the oily product and the combination washed with water followed by brine. The ethereal solution was dried (Na2SO4), concentrated and distilled to provide 34.5 g of the title compound, bp 72°-77° (0.03 mm).

1. temperatureunder reflux for 9 hours
2. temperatureThe mixture was cooled
3. stirringthe resulting mixture was stirred
4. temperatureat reflux for 2 hours under a gentle stream of nitrogen
5. temperatureThe mixture was cooled
6. customthe oily organic layer separated
7. extractionextracted with 3×50 ml portions of diethyl ether
8. washthe combination washed with water
9. dry with materialThe ethereal solution was dried (Na2SO4)
10. concentrationconcentrated
11. distillationdistilled

ORD record

ord-61709937c9834d7786064f8ee101d6f8

Source dataset

uspto-grants-1984_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04458079