反应详情

温度

60 °C

Solid 108 (1.6 g, 5.1 mmol) was gradually added to chlorosulfonic acid (6.0 mL, 90 mmol) with ice bath cooling. The mixture was then heated to 60° C. for 2 h, and the reaction was quenched by pouring slowly, with stirring, into ice-water. The precipitated solid was collected, washed with water, dried and chromatographed on silica gel. Elution with EtOAc/petroleum ether (from 1:4 to 1:1) gave 1-(chloromethyl)-3-(trifluoroacetyl)-1,2-dihydro-3H-benzo[e]indole-7-sulfonyl chloride (113) (0.53 g, 25%) as a pale yellow solid: mp (EtOAc/petroleum ether) 189-192° C.; 1H NMR (CDCl3) δ 8.70-8.64 (m, 2H), 8.13-8.08 (m, 2H), 8.00 (d, J=9.0 Hz, 1H), 4.72-4.68 (m, 1H), 4.55-4.48 (m, 1H), 4.33-4.25 (m, 1H), 3.98-3.93 (m, 1H), 3.68-3.61 (m, 1H), 13C NMR δ 154.9 (q, JC-F 38.4 Hz), 143.9, 140.7, 132.7, 131.8, 130.1, 130.0, 125.8, 124.8, 123.2, 119.6, 115.9 (q, JC-F 288 Hz), 52.8, 45.4, 42.4. Anal. (C15H10Cl2F3NO3S) C, H, N, Cl.

1. temperaturecooling
2. customthe reaction was quenched
3. additionby pouring slowly
4. customThe precipitated solid was collected
5. washwashed with water
6. customdried
7. customchromatographed on silica gel
8. washElution with EtOAc/petroleum ether (from 1:4 to 1:1)