N-bromobutanimide → Methyl 2-(4-(bromomethyl)phenyl)acetate

HRID 1492532Notes

Reaction equation

HRID 1492532 reaction equation
[C:1]1([CH3:12])[CH:6]=[CH:5][C:4]([CH2:7][C:8]([O:10][CH3:11])=[O:9])=[CH:3][CH:2]=1.[Br:13]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:13][CH2:12][C:1]1[CH:2]=[CH:3][C:4]([CH2:7][C:8]([O:10][CH3:11])=[O:9])=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 90265Methyl p-tolylacetate

Product 1

HCID 11770640Methyl 2-(4-(bromomethyl)phenyl)acetateYield 33.2%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

Methyl p-tolylacetate (11 g) was dissolved in 250 ml of carbon tetrachloride, followed by addition of 11.7 g of N-bromosuccinimide and 0.15 g of benzoyl peroxide, and refluxed under heating for 2.5 hours. The reaction mixture obtained was cooled, followed by filtration and distillation of the solvent, which was then fractionated at 4 mmHg and 142 to 150 ° C. to produce methyl 4-bromomethylphenylacetate (5.3 g).

Workup

  1. temperaturerefluxed
  2. temperatureunder heating for 2.5 hours
  3. customThe reaction mixture obtained
  4. temperaturewas cooled
  5. filtrationfollowed by filtration and distillation of the solvent, which
  6. customwas then fractionated at 4 mmHg and 142 to 150 ° C.

Sources & evidence

ORD record
ord-ac1c7f16066646c9a81a28c9c2e301d2
Source dataset
uspto-grants-1994_12
Patent number
US05374641

Reaction notes

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