2-Bromo-2-methylpropionyl bromide → Methyl {4-[4-(2-bromo-2-methylpropanoyl)phenyl]bicyclo[2.2.2]oct-1-yl}acetate

Participants

Reaction Conditions

Reaction Steps

To an ice water cooled solution of methyl (4-phenylbicyclo[2.2.2]oct-1-yl)acetate (Intermediate 8; 3.88 g, 15.02 mmol) in DCM (150 mL) was added aluminium chloride (6.01 g, 45.05 mmol) followed by the dropwise addition of 2-bromoisobutyryl bromide (1.86 mL, 15.02 mmol). The reaction mixture was allowed to stir at ˜0° C. for 30 mins then poured onto ice-water (20 mL). The organic phase was separated and the aqueous phase washed with DCM (2×150 mL), the organic washings combined, dried (MgSO4) and concentrated to leave a yellow gum. This was purified on a 120 g Crawford silica cartridge, loading in DCM and eluting with 0-10%-20% isohexane-EtOAc to give the product as a white solid (5.18 g, 12.72 mmol, 85%). 1H NMR (CDCl3) δ 1.64-1.69 (6H, m), 1.83-1.88 (6H, m), 2.03 (6H, s), 2.18 (2H, s), 3.66 (3H, s), 7.36 (2H, d), 8.10 (2H, d); Solid Probe MS m/e M+ 407.

Provenance & Evidence