Acetic Acid → (3-chloro-5-fluoro-phenyl)-acetic Acid Methyl Ester

HRID 547028Notes

Reaction equation

HRID 547028 reaction equation
C[Si](C=[N+]=[N-])(C)C.[Cl:8][C:9]1[CH:10]=[C:11]([CH2:16][C:17]([OH:19])=[O:18])[CH:12]=[C:13]([F:15])[CH:14]=1.[C:20](O)(=O)C>CO.C1(C)C=CC=CC=1>[CH3:20][O:18][C:17](=[O:19])[CH2:16][C:11]1[CH:12]=[C:13]([F:15])[CH:14]=[C:9]([Cl:8])[CH:10]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 167693TrimethylsilyldiazomethaneHCID 27348372-(3-Chloro-5-fluorophenyl)acetic acid

Product 1

HCID 57443518(3-chloro-5-fluoro-phenyl)-acetic Acid Methyl EsterYield 99%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

Trimethylsilyldiazomethane (2 M solution in diethyl ether, 0.199 mL, 0.398 mmol) was added to a solution of (3-chloro-5-fluoro-phenyl)acetic acid (50 mg, 0.265 mmol) in methanol (0.5 mL) and toluene (2 mL), and the mixture was stirred at room temperature for 10 minutes. Acetic acid was added to the reaction mixture to terminate the reaction, and then the mixture was concentrated under reduced pressure to give the target compound as a colorless oil (53 mg, 99%).

Workup

  1. customto terminate
  2. customthe reaction
  3. concentrationthe mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-39cb5eed227e4ff6b2ea509c8be8ddc8
Source dataset
uspto-grants-2011_05
Patent number
US07935688B2

Reaction notes

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