Bromine → 4,7-dibromo-3,4-dihydrobenzo[b]oxepin-5(2H)-one

HRID 1498058노트

반응식

HRID 1498058 반응식
[Br:1][C:2]1[CH:13]=[CH:12][C:5]2[O:6][CH2:7][CH2:8][CH2:9][C:10](=[O:11])[C:4]=2[CH:3]=1.[Br:14]Br>CCOCC>[Br:14][CH:9]1[CH2:8][CH2:7][O:6][C:5]2[CH:12]=[CH:13][C:2]([Br:1])=[CH:3][C:4]=2[C:10]1=[O:11]

참가 물질

4

반응물 2

HCID 24408BromineHCID 106815487-Bromo-3,4-dihydro-1-benzoxepin-5(2H)-one

생성물 1

HCID 579004584,7-dibromo-3,4-dihydrobenzo[b]oxepin-5(2H)-one수율 91.9%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

To 7-bromo-3,4-dihydrobenzo[b]oxepin-5(2H)-one (3 g, 12 mmol) in ether (110 mL) was added bromine (0.7 mL, 14 mmol) and allowed to stir at room temperature overnight. The reaction mixture was concentrated under reduced pressure and purified via ISCO chromatography (hexane to 20% hexane in EtOAc over 45 minutes). Collected fractions and concentrated to give 4,7-dibromo-3,4-dihydrobenzo[b]oxepin-5(2H)-one (3.53 g, 89%). 1H NMR (500 MHz, CDCl3) δ 7.86 (d, J=2.5, 1H), 7.52 (dt, J=28.5, 14.2, 1H), 6.97 (d, J=8.7, 1H), 4.95 (dd, J=7.6, 6.8, 1H), 4.53-4.36 (m, 1H), 4.17 (ddd, J=12.8, 9.9, 4.4, 1H), 3.04-2.84 (m, 1H), 2.52 (ddt, J=14.7, 7.8, 4.5, 1H)

후처리

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. custompurified via ISCO chromatography (hexane to 20% hexane in EtOAc over 45 minutes)
  3. concentrationCollected fractions and concentrated

출처 및 근거

ORD 기록
ord-2d2cb4bff7f242e29b075b73248c2757
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09198918B2

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