Allyl bromide → HCID 178440464, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of indium powder (0.68 g, 5.9 mmol) in anhydrous N,N-dimethylformamide (2 mL) at 0° C. was added allylbromide (0.76 mL, 8.8 mmol) dropwise over 5 min. The cooling bath was removed and the resulting exothermic reaction was allowed to stir for several minutes, during which time the indium metal dissolved. The resulting solution was cooled to 0° C., and a solution of Example 7A (1.00 g, 4.9 mmol) in anhydrous N,N-dimethylformamide (8 mL) was added. The resulting solution was allowed to warm to rt and stirred 1 h. The reaction mixture was partitioned between H2O (50 mL) and ethyl acetate (3×50 mL), and the combined organic layers were dried over Na2SO4. The solution was filtered and concentrated, and the product was precipitated from diethyl ether to provide the title compound as a light tan powder (0.99 g, 82%). 1H NMR (300 MHz, DMSO-d6) δ ppm 11.84 (s, 1H), 7.85 (d, J=7.7 Hz, 2H), 7.60 (t, J=7.4 Hz, 1H), 7.32-7.48 (m, 1H), 7.14 (br s, 1H), 5.68 (br s, 1H), 5.09 (m, 1H), 4.64-4.81 (m, 2H), 3.11 (s, 3H), 2.20-2.45 (m, 2H).

Provenance & Evidence