N-bromobutanimide → 4-Bromo-2-methylpent-2-enoic acid methyl ester

HRID 2245774Notes

Reaction equation

HRID 2245774 reaction equation
[CH3:1][O:2][C:3](=[O:9])[C:4]([CH3:8])=[CH:5][CH2:6][CH3:7].[Br:10]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[CH3:1][O:2][C:3](=[O:9])[C:4]([CH3:8])=[CH:5][CH:6]([Br:10])[CH3:7]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 4056868Methyl 2-methyl-2-pentenoate

Product 1

HCID 5813134-Bromo-2-methylpent-2-enoic acid methyl esterYield 82.5%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of 2-methylpent-2-enoic acid methyl ester (1.20 g, 9.37 mmol) and N-bromosuccinimide (1.83 g, 10.2 mmol) in dry carbon tetrachloride (15 mL) irradiated with a 250 W sunlamp so as to achieve a state of reflux for 2.5 hours. After cooling, the succinimide was filtered off, the carbon tetrachloride was evaporated, and the product was distilled over a short path under reduced pressure to give the title compound (1.60 g, 82%) as a colourless oil.

Workup

  1. temperatureof reflux for 2.5 hours
  2. temperatureAfter cooling
  3. filtrationthe succinimide was filtered off
  4. customthe carbon tetrachloride was evaporated
  5. distillationthe product was distilled over a short path under reduced pressure

Sources & evidence

ORD record
ord-9367ab6252674b62af7d4950fd4bc8dd
Source dataset
uspto-grants-2010_03
Patent number
US07683185B2

Reaction notes

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