Hydrogen Bromide → 3-Bromoacetyl-5,6,7,8-tetrahydroisoquinoline

Participants

Reaction Steps

To a mixture of 3-acetyl-5,6,7,8-tetrahydroisoquinoline (287.7 mg, 1.64 mmol) and hydrobromic acid (25% solution in acetic acid, 3.1 ml) was added a solution of bromine (93.3 μl, 1.81 mmol) in acetic acid (0.4 ml) at 0° C. The mixture was stirred at room temperature for an additional 3 h. and concentrated. The residue was made basic with saturated aqueous hydrogen bicarbonate and extracted with diethyl ether (150 ml). The organic layer dried (MgSO4) and concentrated to afford 524.9 mg of the crude title compound as an brown oil.

Provenance & Evidence