Methanol → Methyl alpha-bromo-2-chlorophenylacetate

HRID 1015682Notes

Reaction equation

HRID 1015682 reaction equation
[Br:1][CH:2]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[Cl:12])[C:3]([OH:5])=[O:4].S(=O)(=O)(O)O.O.[CH3:19]O>>[CH3:19][O:4][C:3](=[O:5])[CH:2]([Br:1])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[Cl:12]

Participants

5

Procedure

α-Bromo-2-chlorophenyl acetic acid (350.0 gm) was dissolved in methanol (1.18 Liter) and concentrated sulphuric acid (53.20 gm) was added. The reaction mixture was refluxed for 4 hours. After completion of the reaction, the reaction mixture was distilled out to get a syrupy mass. To the residual mass, water (560 ml) was added and the product was extracted into chloroform (560 ml). The chloroform layer was separated and was treated with 10% aqueous sodium bicarbonate solution (1.12 Litre). The chloroform extract was finally washed with water and chloroform was distilled out to get a syrupy mass to get the titled compound.

Workup

  1. temperatureThe reaction mixture was refluxed for 4 hours
  2. customAfter completion of the reaction
  3. distillationthe reaction mixture was distilled out
  4. customto get a syrupy mass
  5. extractionthe product was extracted into chloroform (560 ml)
  6. customThe chloroform layer was separated
  7. additionwas treated with 10% aqueous sodium bicarbonate solution (1.12 Litre)
  8. extractionThe chloroform extract
  9. washwas finally washed with water and chloroform
  10. distillationwas distilled out
  11. customto get a syrupy mass

Sources & evidence

ORD record
ord-9c9a34bab362438d974081516afad4e4
Source dataset
uspto-grants-2011_07
Patent number
US07985859B2

Reaction notes

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