3,5-Dibromophenol → HCID 20735476, compound

Temperature

20 °C

A solution of 3,5-dibromophenol (prepared according to Recl. Trav. Chim. Pays-Bas. 1908, 27, 30) (10.08 g, 40 mmol) and diethylthiocarbamyl chloride (7.9 g, 52 mmol) in 1-methyl-2-pyrrolidinone (80 ml) was cooled to 0° C. under an atmosphere of nitrogen. Sodium hydride (60% dispersion in mineral oil, 1.92 g, 48 mmol) was added portionwise with stirring. The mixture was allowed to warm to 20° C. and stirred under nitrogen for two hours. The mixture was partitioned between diethyl ether (250 ml) and water (350 ml) and the aqueous layer was further extracted with diethyl ether (250 ml then 100 ml). The organic layers were combined, washed with water (150 ml) and brine (150 ml), dried over magnesium sulphate, filtered and concentrated under reduced pressure to leave a yellow solid. The crude product was purified by flash chromatography on silica gel eluting with dichloromethane:pentane (1:1, by volume) to provide the title compound (13.4 g) as a white solid, m.p. 72–74° C.

1. stirringstirred under nitrogen for two hours
2. customThe mixture was partitioned between diethyl ether (250 ml) and water (350 ml)
3. extractionthe aqueous layer was further extracted with diethyl ether (250 ml
4. washwashed with water (150 ml) and brine (150 ml)
5. dry with materialdried over magnesium sulphate
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure
8. customto leave a yellow solid
9. customThe crude product was purified by flash chromatography on silica gel eluting with dichloromethane:pentane (1:1, by volume)

ORD record

ord-1bf5cd62979f427285178170151d601e

Source dataset

uspto-grants-2006_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07141585B2