1,1-Dibromoethane → HCID 20484457, compound

Participants

Reaction Steps

A solution of sodium hydroxide (21 g) in water (75 ml) was added to 2-methoxy-5-methyl-4-methylsulphinylphenol (21 g), dibromoethane (160 ml) and benzyltriethylammonium chloride (1.26 g) and the resultant mixture heated at 60° for 18 hours. After cooling, water (50 ml) was added. The organic layer was separated, the aqueous layer extracted with dibromoethane (2×10 ml). The combined organic extracts were washed with 2 N aqueous sodium hydroxide solution (100 ml) and water (100 ml) and the solvent was evaporated under reduced pressure to give an orange oil, which on trituration with 40°-60° petroleum ether afforded a solid, which was filtered off, washed with further petroleum ether and dried in vacuo. The crude mono-ether (29.24 g), m.p. 66°-67° was used without further purification in the next stage. (A sample purified by column chromatography on Florisil eluting with dichloromethane followed by crystallisation from diethyl ether/40°-60° petroleum ether (1:3 v/v) had m.p. 72°-73°).

Provenance & Evidence