tert-Butyl methyl ether → HCID 23001232, compound

Participants

Reaction Steps

A solution of bromine (0.56 ml, 10.90 mmol) in DCM (30 ml) was added dropwise to a solution of ((4-(methoxy)cyclohex-3-enyloxy)methyl)benzene (3.4 g, 15.57 mmol), which was prepared as described in the last step, in DCM (100 ml). The reaction mixture was stirred for 1 hour at room temperature. Tert-butyl methyl ether (150 ml) was added. The solution was washed with ice cooled water (200 ml), a saturated aqueous solution of sodium thiosulphate (100 ml), and a saturated aqueous solution of sodium hydrogencarbonate. The organic layer was dried over magnesium sulphate. The solvent was removed in vacuo. The crude product was purified by flash chromatography on silica (90 g), using ethyl acetate/heptane (1:2) as eluent, to give 1.40 g of a mixture of diastereoisomeres of 4-benzyloxy-2-bromocyclohexanone.

Provenance & Evidence