Dibromomethane → HCID 67403052, compound

Participants

Reaction Steps

A drop of acetyl bromide (1 drop) was added to a mixture of activated (with 1N HCl) zinc (19.6 g, 0.3 mol), cuprous bromide (1.5 g, 0.01 mol) and 1-((1S)-2,2,3-trimethylcyclopent-3-enyl)ethanol (ca. 20% ee, 15.4 g, 0.3 mol) in diethyl ether (50 ml). After 10 minutes stirring, dibromomethane (52.0 g, 0.3 mol) was added and stirring at reflux continued for 6 h. The solid was filtered off and washed with MTBE. The combined organic phases were washed with water and diluted citric acid solution, dried (MgSO4), concentrated in vacuo and distilled using a 5 cm Widmer-column to give 1-((3S)-1,2,2-trimethylbicyclo[3.1.0]hex-3-yl)ethanol (2.1 g, 12.5% yield, colourless liquid; GC/MS: 3 main diastereomeric pairs of enantiomers 33+30.5+20%). Analytical samples of the three main pairs of enantiomers were obtained by flash chromatography (MTBE/hexane 1:3)

Provenance & Evidence