Sodium Hydroxide → 3,5-Dibromobenzene-1-thiol

Temperature

20 °C

Sodium hydroxide (1.96 g, 49 mmol) was added to a solution of S-(3,5-dibromophenyl) diethylthiocarbamate (12 g, 32.7 mmol) (Preparation 47) in methanol (33 ml) and the mixture was heated at reflux for 15 hours. The mixture was cooled to 20° C. and concentrated under reduced pressure. The residue was partitioned between dichloromethane (90 ml) and water (250 ml) and the aqueous layer was further extracted with dichloromethane (90 ml). The combined organic layers were washed with a solution of sodium hydroxide (1N, 100 ml). The combined aqueous layers were cooled to 0° C. and the pH was adjusted to 2 by the addition of concentrated hydrochloric acid, giving a white suspension. This suspension was extracted with dichloromethane (2×250 ml) and the combined extracts were washed with brine (25 ml), dried over magnesium sulphate, filtered and concentrated under reduced pressure to leave the title compound as a yellow solid (6.7 g).

1. temperaturethe mixture was heated
2. temperatureat reflux for 15 hours
3. concentrationconcentrated under reduced pressure
4. customThe residue was partitioned between dichloromethane (90 ml) and water (250 ml)
5. extractionthe aqueous layer was further extracted with dichloromethane (90 ml)
6. washThe combined organic layers were washed with a solution of sodium hydroxide (1N, 100 ml)
7. temperatureThe combined aqueous layers were cooled to 0° C.
8. additionthe pH was adjusted to 2 by the addition of concentrated hydrochloric acid
9. customgiving a white suspension
10. extractionThis suspension was extracted with dichloromethane (2×250 ml)
11. washthe combined extracts were washed with brine (25 ml)
12. dry with materialdried over magnesium sulphate
13. filtrationfiltered
14. concentrationconcentrated under reduced pressure

ORD record

ord-1bfc52ec980e4bc991444d5ac2c59569

Source dataset

uspto-grants-2006_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07141585B2