Methanol → Methyl 2-(2-bromo-5-chlorophenyl)acetate

HRID 2415539Notes

Reaction equation

HRID 2415539 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[CH2:9][C:10]([OH:12])=[O:11].S(=O)(=O)(O)O.[CH3:18]O>>[CH3:18][O:11][C:10](=[O:12])[CH2:9][C:3]1[CH:4]=[C:5]([Cl:8])[CH:6]=[CH:7][C:2]=1[Br:1]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 27355502-(2-Bromo-5-chlorophenyl)acetic acid

Product 1

HCID 22640779Methyl 2-(2-bromo-5-chlorophenyl)acetate

Procedure

A solution of (2-bromo-5-chlorophenyl)acetic acid (1-1) (15.0 g, 60.1 mmol) and concentrated sulfuric acid (0.150 mL of a 36N solution) in methanol (120 mL) was heated at reflux for approximately 15 h. After cooling to room temperature, the reaction mixture was concentrated in vacuo and the residue partitioned between methylene chloride and saturated aqueous sodium bicarbonate. The organic layer was separated and the aqueous phase re-extracted twice with methylene chloride. The combined organic extracts were washed with water, brine, dried (MgSO4) and the volatiles evaporated. The residual colorless liquid (15.9 g) was used without further purification in the Step C below.

Workup

  1. temperatureat reflux for approximately 15 h
  2. concentrationthe reaction mixture was concentrated in vacuo
  3. customthe residue partitioned between methylene chloride and saturated aqueous sodium bicarbonate
  4. customThe organic layer was separated
  5. extractionthe aqueous phase re-extracted twice with methylene chloride
  6. washThe combined organic extracts were washed with water, brine
  7. dry with materialdried (MgSO4)
  8. customthe volatiles evaporated
  9. customThe residual colorless liquid (15.9 g) was used without further purification in the Step C below

Sources & evidence

ORD record
ord-f5894ac6c85644e194264894d8f4d8d1
Source dataset
uspto-grants-2004_11
Patent number
US06818658B2

Reaction notes

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