Water → 1-(bromoacetyl)-5-(methyloxy)-6-nitro-2,3-dihydro-1H-indole

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Reaction Conditions

Reaction Steps

A solution of 5-(methyloxy)-6-nitro-2,3-dihydro-1H-indole (33.6 g, 173 mmol) in CH.2Cl2 (150 mL) was added dropwise to a mixture of bromoacetylchloride (54.5 g, 346 mmol) and K2CO3 (53.0 g, 381 mmol) in CH2Cl2 (150 mL). The resulting solution was stirred at 0° C. for 1 hour, then warmed up RT for 4 hours. Water (150 mL) was added and the mixture was extracted with CH2Cl2 (2×100 mL). The organic phase was dried over Na2SO4, the solvent was removed to yield the 1-(bromoacetyl)-5-(methyloxy)-6-nitro-2,3-dihydro-1H-indole (54.2 g, 99%). 1HNMR (400 MHz, DMSO) δ ppm 2.47(s, 2H), 3.25 (m, 2 H), 3.87 (s, 3 H), 4.21 (m, 2 H), 7.34 (s, 1 H), 8.42 (s, 1 H).

Provenance & Evidence