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

HRID 886002ノート

反応式

HRID 886002 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-6cb706e200c444feb577f7de32a39f20
出典データセット
uspto-grants-2012_08
特許番号
US08242104B2

反応ノート

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