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 (536 mg, 2.07 mmol) in DCM (30 mL) was added aluminum chloride (830 mg, 6.22 mmol) followed by the dropwise addition of 2-bromoisobutyryl bromide (0.25 mL, 2.07 mmol). The reaction mixture was allowed to stir at ˜0° C. for 1 hr, then poured onto ice-water (˜20 mL). The organic phase was separated and the aqueous phase washed with DCM (3×150 mL), the organic were combined, dried (MgSO4) and concentrated to leave a yellow gum. This was purified on a 12 g silicyle silca cartridge, loading in DCM and eluting 0-10%-20% isohexane-EtOAc, to provide the title compound as a red solid, 648 mg (1.59 mmol, 77%); 1H NMR (CDCl3) δ 1.65-1.69 (m, 6H), 1.84-1.88 (m, 6H), 2.03 (s, 6H), 2.18 (s, 2H), 3.66 (s, 3H), 7.36 (d, 2H), 8.09 (d, 2H); MS m/e MH+ 377 (M−OMe).

Provenance & Evidence