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

HRID 60069

Reaktionsgleichung

Reaktionsgleichung von HRID 60069
[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]

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-d70815b909984374ab7691bac5ee084a
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09440957B2

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