Carbon tetrabromide → Indole-bromide

Participants

Reaction Steps

7-Hydroxymethyl-2-methyl-3,7,8,9-tetrahydro-pyrano[3,2-e]indole-1-carboxylic acid benzyl ester (0.410 g, 1.16 mmol, 1 eq) was suspended in dry CH2Cl2 (20 mL) under Ar. Carbon tetrabromide (0.615 g, 1.86 mmol, 1.6 eq) was added followed by the addition of triphenylphosphine (0.441 g, 1.5 mmol, 1.3 eq). The reaction mixture was stirred at room temperature. The reaction was followed by TLC (CH2Cl2/MeOH 9/1). After 3 hours, the reaction mixture was loaded on silica gel and chromatographed, eluting with CH2Cl2/MeOH 9/1. 0.191 g (40% yield) of the indole-bromide was obtained as an unstable brown oil.

Provenance & Evidence