반응 #794971

반응 방정식

8-bromo-3,4-dihydro-2H-benzo[b]oxepin-5-one

Br2

→

4,8-dibromo-3,4-dihydrobenzo[b]oxepin-5(2H)-one

수율 102.5%

용매

Et2O

반응 조건

후처리

1. 1
   기타Volatiles were evaporated
2. 2
   기타the residue purified by flash column chromatography (0-20% EtOAc in hexanes)

실험 절차

To a stirred solution of 8-bromo-3,4-dihydro-2H-benzo[b]oxepin-5-one (3.10 g; 12.8 mmol) in Et2O at 0° C. was added Br2 (625 μl; 12.2 mmol) and the reaction mixture was allowed to warm to r.t. over 2 h. Volatiles were evaporated and the residue purified by flash column chromatography (0-20% EtOAc in hexanes) to give 4,8-dibromo-3,4-dihydrobenzo[b]oxepin-5(2H)-one as a colorless solid (4.0 g, 96% yield). 1H NMR (400 MHz, CDCl3) δ 7.18-7.21 (m, 2H), 7.55 (d, J=8.0, 1H), 4.87 (app. t, J=5.2, 2H), 4.33-4.39 (m, 1H), 4.09-4.16 (m, 1H), 2.78-2.91 (m, 1H), 2.40-2.49 (m, 1H).

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