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

HRID 60069

Reaction equation

HRID 60069 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-d70815b909984374ab7691bac5ee084a
Source dataset
uspto-grants-2016_09
Patent number
US09440957B2

Linked notes

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