Hydrogen Bromide → Methyl alpha-Bromo-alpha-[p-(p-chlorophenoxy)phenyl]acetate

HRID 1863274Notes

Reaction equation

HRID 1863274 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([CH2:13][C:14]([O:16][CH3:17])=[O:15])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.[Br:20]N1C(=O)CCC1=O.Br>C(Cl)(Cl)(Cl)Cl>[Br:20][CH:13]([C:10]1[CH:11]=[CH:12][C:7]([O:6][C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:19][CH:18]=2)=[CH:8][CH:9]=1)[C:14]([O:16][CH3:17])=[O:15]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 67184N-bromobutanimideHCID 12531835HCID 12531835, compound

Product 1

HCID 20392594Methyl alpha-Bromo-alpha-[p-(p-chlorophenoxy)phenyl]acetate

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 1.38 g of methyl α-[p-(p-chlorophenoxy)phenyl]acetate in 15 ml of carbon tetrachloride is added 0.92 g of N-bromosuccinimide and a small drop of concentrated HBr. The mixture is maintained at reflux for 72 hours and cooled to room temperature. Filtration through 50 g of aluminum oxide, evaporation of the solvent and bulb-to-bulb distillation of the residue (166° @ 0.05 mm) affords the product as a colorless oil.

Workup

  1. temperatureThe mixture is maintained
  2. temperatureat reflux for 72 hours
  3. filtrationFiltration
  4. customthrough 50 g of aluminum oxide, evaporation of the solvent and bulb-to-bulb distillation of the residue (166° @ 0.05 mm)

Sources & evidence

ORD record
ord-d892a64dd6bb42f0aa12b3a5597b66a8
Source dataset
uspto-grants-1979_09
Patent number
US04168385

Reaction notes

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