N-bromobutanimide → 3-Bromomethyl-5-chlorophenylethyl acetate

HRID 420553Notes

Reaction equation

HRID 420553 reaction equation
[C:1]([O:4][CH2:5][CH2:6][C:7]1[CH:12]=[C:11]([CH3:13])[CH:10]=[C:9]([Cl:14])[CH:8]=1)(=[O:3])[CH3:2].[Br:15]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[C:1]([O:4][CH2:5][CH2:6][C:7]1[CH:8]=[C:9]([Cl:14])[CH:10]=[C:11]([CH2:13][Br:15])[CH:12]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 666578653-Chloro-5-methylphenylethyl acetate

Product 1

HCID 666577833-Bromomethyl-5-chlorophenylethyl acetate

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 3-chloro-5-methylphenylethyl acetate (0.20 g; 0.958 mol), N-bromosuccinimide (0.21 g; 1.21 mmol) and 2,2-azobis(isobutyronitrile) (0.01 g; 0.037 mmol) in carbon tetrachloride (2 ml) were refluxed for 2 hours. After cooling and filtration of the precipitate, the filtrate was condensed under reduced pressure. The residue was purified by column chromatograph on silica gel (hexane:ethyl acetate=20:1) to give 3-bromomethyl-5-chlorophenylethyl acetate as colorless oil (0.16 g; 57%).

Workup

  1. temperaturewere refluxed for 2 hours
  2. temperatureAfter cooling
  3. filtrationfiltration of the precipitate
  4. customcondensed under reduced pressure
  5. customThe residue was purified by column chromatograph on silica gel (hexane:ethyl acetate=20:1)

Sources & evidence

ORD record
ord-a1ccb0c22e044abbbd491403b280921b
Source dataset
uspto-grants-2012_01
Patent number
US08097610B2

Reaction notes

Loading…