Benzoyl Peroxide → tert-butyl (2E)-4-bromobut-2-enoate

HRID 60069

反応式

HRID 60069 の反応式
[C:1]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])(=[O:5])/[CH:2]=[CH:3]/[CH3:4].C1C(=O)N([Br:18])C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:18][CH2:4]/[CH:3]=[CH:2]/[C:1]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5]

参加物

5

反応物 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 5463127tert-Butyl Crotonate

生成物 1

HCID 11806237tert-butyl (2E)-4-bromobut-2-enoate

試薬・触媒・溶媒 1

HCID 5943Carbon Tetrachloride溶媒

実験手順

To the mixture of (E)-tert-butyl but-2-enoate (10.0 g, 70.4 mmol) and NBS (12.5 g, 70.4 mmol) in CCl4 (150 mL) was added benzoyl peroxide (510 mg, 2.11 mmol), and the reaction was refluxed for 12 h. The mixture was cooled to room temperature, and the solid was filtered off. The filtrate was concentrated in vacuo, and purified by column chromatography to afford (E)-tert-butyl 4-bromobut-2-enoate (I-2a). 1H-NMR (400 MHz, CDCl3) δ 7.02-6.76 (m, 1H), 6.05-5.89 (m, 1H), 4.06-3.95 (m, 2H), 1.56-1.40 (m, 9H). MS calculated for C8H14BrO2 (M+H+) 221.01. found: 221.0.

後処理

  1. temperaturethe reaction was refluxed for 12 h
  2. filtrationthe solid was filtered off
  3. concentrationThe filtrate was concentrated in vacuo
  4. custompurified by column chromatography

出典と根拠

ORDレコード
ord-d70815b909984374ab7691bac5ee084a
出典データセット
uspto-grants-2016_09
特許番号
US09440957B2

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