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

HRID 1498058ノート

反応式

HRID 1498058 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

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)

後処理

  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

出典と根拠

ORDレコード
ord-2d2cb4bff7f242e29b075b73248c2757
出典データセット
uspto-grants-2015_12
特許番号
US09198918B2

反応ノート

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