O-Cresol → 3-Fluoromethoxy-2-[2-(2-methylphenoxymethyl)phenyl]-acrylic acid methyl ester

HRID 726852Notes

Reaction equation

HRID 726852 reaction equation
[CH3:1][O:2][C:3](=[O:17])[C:4]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15]Br)=[CH:5][O:6][CH2:7][F:8].[C:18]1([CH3:25])[C:23]([OH:24])=[CH:22][CH:21]=[CH:20][CH:19]=1.C([O-])([O-])=O.[K+].[K+].C1OCCOCCOCCOCCOCCOC1>C(#N)C.O>[CH3:1][O:2][C:3](=[O:17])[C:4]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][O:24][C:23]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH3:25])=[CH:5][O:6][CH2:7][F:8]

Participants

7

Reactant 4

HCID 335O-CresolHCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 543314062-(2-Bromomethylphenyl)-3-fluoromethoxyacrylic acid methyl ester

Product 1

HCID 542988973-Fluoromethoxy-2-[2-(2-methylphenoxymethyl)phenyl]-acrylic acid methyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of 1.66 g of 2-(2-bromomethylphenyl)-3-fluoromethoxyacrylic acid methyl ester, 0.65 g of o-cresol, 1.38 g of pulverized potash and 0.07 g of 18-crown-6 in 15 ml of acetonitrile is stirred at room temperature for 24 hours. Water is then added, the reaction mixture is acidified with 1N hydrochloric acid and extraction is carried out with ethyl acetate. The combined organic phases are dried over sodium sulfate, filtered and concentrated by evaporation. Chromatography on silica gel with hexane/ethyl acetate yields pure 3-fluoromethoxy-2-[2-(2-methylphenoxymethyl)phenyl]-acrylic acid methyl ester in the form of a viscous oil.

Workup

  1. extractionthe reaction mixture is acidified with 1N hydrochloric acid and extraction
  2. dry with materialThe combined organic phases are dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-ba75d6a978c54a1e9530b4c5897fbab3
Source dataset
uspto-grants-1998_01
Patent number
US05710314

Reaction notes

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