Water → HCID 19780354, compound

Participants

Reaction Conditions

Reaction Steps

5,10-Dihydro-2-methoxy-1,3-dimethyl-8-isopropylindeno[1,2-b]indole (0.50 g, 1.64 mmol) was dissolved in dry dichloromethane (DCM, 2 cm3) under anhydrous conditions and cooled to -78° C. Boron tribromide (2 cm3 1.2 eq of 1 M solution in DCM) was added, and warmed to room temperature, whereupon a suspension formed. After 20 minutes, this had re-dissolved. Water (2 cm3) was cautiously added, and the mixture extracted between more DCM, and saturated sodium bicarbonate solution (some solid around during extraction finally dissolved). The DCM layer was dried (Na2SO4) and filtered through a pad of "flash" silica, eluting with DCM to yield a white solid (0.43 g, 90%) M.p. 173° C.(dec.). 1H NMR (CDCl3)δ: 8.04 (1H, br), 7.43 (1H, br), 7.29 (1H, d, J=8.2), 7.04 (1H, br), 4.58 (1H, br), 3.55 (2H, br), 30.2 (1H, septet, J=7.0Hz, 2.30 (3H, s), 2.29 (3H,s), 1.33 (6H, d, J=7.0Hz).

Provenance & Evidence