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

HRID 60069노트

반응식

HRID 60069 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 5943Carbon Tetrachloride용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-d70815b909984374ab7691bac5ee084a
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09440957B2

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