Water → Methyl 2,5-difluoro-4-[(3-methoxyphenoxy)methyl]benzoate

HRID 508437Notes

Reaction equation

HRID 508437 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1.Br[CH2:11][C:12]1[C:21]([F:22])=[CH:20][C:15]([C:16]([O:18][CH3:19])=[O:17])=[C:14]([F:23])[CH:13]=1.C(=O)([O-])[O-].[K+].[K+].O>CS(C)=O>[F:23][C:14]1[CH:13]=[C:12]([CH2:11][O:9][C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=2)[C:21]([F:22])=[CH:20][C:15]=1[C:16]([O:18][CH3:19])=[O:17]

Participants

6

Reactant 4

HCID 962WaterHCID 90073-MethoxyphenolHCID 11430Potassium CarbonateHCID 66666576Benzoic acid, 4-(bromomethyl)-2,5-difluoro-, methyl ester

Product 1

HCID 86682556Methyl 2,5-difluoro-4-[(3-methoxyphenoxy)methyl]benzoate

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 3-methoxyphenol (221 mg, 1.8 mmol) in DMSO (5 mL) was added methyl 4-(bromomethyl)-2,5-difluorobenzoate (Preparation 27, 491 mg, 1.8 mmol) followed by potassium carbonate (491 mg, 3.5 mmol) and the reaction mixture was stirred at room temperature under nitrogen for 18 hours. The mixture was poured into water and extracted with EtOAc (3×20 mL), washed with 1 M aqueous NaOH and water, dried over magnesium sulphate and the solvent removed under reduced pressure to yield the title compound as a solid, which was taken to the next step without further purification (441 mg, 81%).

Workup

  1. extractionextracted with EtOAc (3×20 mL)
  2. washwashed with 1 M aqueous NaOH and water
  3. dry with materialdried over magnesium sulphate
  4. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-ed960c60121244c994a178b7a853eec0
Source dataset
uspto-grants-2015_08
Patent number
US09096500B2

Reaction notes

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