Water → Methyl 4-bromo-2-chlorobenzeneacetate

HRID 1641534Notes

Reaction equation

HRID 1641534 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[C:4]([Cl:12])[CH:3]=1.[C:13](=O)([O-])[O-].[K+].[K+].IC.O>CN(C)C=O>[CH3:13][O:10][C:9](=[O:11])[CH2:8][C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][C:4]=1[Cl:12]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 53403617(4-Bromo-2-chlorophenyl)acetic acid

Product 1

HCID 57624630Methyl 4-bromo-2-chlorobenzeneacetateYield 102.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-bromo-2-chlorophenylacetic acid (240 g) of Reference Example 15 in N,N-dimethylformamide (3000 mL) were added potassium carbonate (399 g) and iodomethane (164 g) at 7° C., and the mixture was stirred at the same temperature for 3 hr and stirred at room temperature for 19 hr. The reaction mixture was poured into water, and partitioned and extracted with ethyl acetate. The organic layer was washed 3 times with 25% brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give the title compound (259 g) as a brown oil.

Workup

  1. stirringstirred at room temperature for 19 hr
  2. custompartitioned
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed 3 times with 25% brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-b00b01ea797248cab5ae2490c0dd9845
Source dataset
uspto-grants-2012_02
Patent number
US08114902B2

Reaction notes

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