1-Bromo-1-methylcyclopropane → Cyclopropylmethyl-p-toluenethiosulfonate

Participants

Reaction Conditions

Reaction Steps

To a solution of methylcyclopropyl bromide (4.00 g, 29.6 mmol) in ethanol (20.0 mL) was added potassium thiotosylate (10.0 g, 44.4 mmol) and the mixture heated to 90° C. for 10 h. The mixture was then quenched into a 1:1 mixture of H2O (50.0 mL) and diethyl ether (50.0 mL). The layers were separated and the organic layer washed with brine (50.0 mL). The organic layer was then dried with MgSO4 and concentrated in vacuo to yield the title compound as a solid (5.2 g, m.p. 46°-48° C.). 1H NMR (400 MHz, CDCl3) δ 7.816 (d, 2 H, J=8.8 Hz), 7.308 (d, 2 H, J=8.8 Hz), 2.945 (d, 2 H, J=7.6 Hz), 2.451 (s, 3 H), 1.010-0.933 (m, 1 H), 0.592-0.545 (m, 2 H), 0.236-0.197 (m, 2 H).

Provenance & Evidence