Chloromethyl Methyl Ether → 3-Bromo-5-fluoro-4-methoxymethoxybenzoic acid methyl ester

HRID 423244Notes

Reaction equation

HRID 423244 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[C:8]([F:10])[C:7]([OH:11])=[C:6]([Br:12])[CH:5]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:20][O:21][CH2:22]Cl>CC(C)=O.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[C:8]([F:10])[C:7]([O:11][CH2:20][O:21][CH3:22])=[C:6]([Br:12])[CH:5]=1

Participants

6

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 11430Potassium CarbonateHCID 57467610HCID 57467610, compound

Product 1

HCID 586297383-Bromo-5-fluoro-4-methoxymethoxybenzoic acid methyl esterYield 81.1%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-bromo-5-fluoro-4-hydroxybenzoic acid methyl ester (637 mg) in acetone (7 mL) were added potassium carbonate (708 mg) and chloromethyl methyl ether (412 mg), and the mixture was stirred at room temperature overnight. The reaction mixture was diluted with ethyl acetate, washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=9:1, v/v) to give the title compound (608 mg).

Workup

  1. washwashed with water and saturated brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by column chromatography on silica gel (hexane

Sources & evidence

ORD record
ord-b88afdcd891b4a598cd288cb275ead05
Source dataset
uspto-grants-2012_01
Patent number
US08101774B2

Reaction notes

Loading…