1,4-Dimethoxybenzene → HCID 86682898, compound

HRID 2368919Notes

Reaction equation

HRID 2368919 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][CH:4]=1.[F:11][C:12]1[CH:13]=[C:14]([CH2:20][C:21](O)=[O:22])[CH:15]=[C:16]([O:18][CH3:19])[CH:17]=1>O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][C:4]=1[C:21](=[O:22])[CH2:20][C:14]1[CH:15]=[C:16]([O:18][CH3:19])[CH:17]=[C:12]([F:11])[CH:13]=1

Participants

4

Reactant 2

HCID 90161,4-DimethoxybenzeneHCID 26985459HCID 26985459, compound

Product 1

HCID 86682898HCID 86682898, compoundYield 26.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 1,4-dimethoxybenzene (2.62 g, 19 mmol) in PPA (10 mL) at room temperature, 2-(3-fluoro-5-methoxyphenyl)acetic acid (2.33 g, 12.6 mmol) was added. The mixture was stirred at 80° C. for 3 h, cooled to room temperature, and then H2O (100 mL) was added. After extraction with ethyl acetate (3×50 mL), the organic phase was dried over Na2SO4, concentrated, and the crude was purified by silica-gel column chromatography (ethyl acetate/petroleum ether=1/4) to give 1.0 g of 1-(2,5-dimethoxyphenyl)-2-(3-fluoro-5-methoxyphenyl)ethanone. LCMS: 305.1 [M+H]+.

Workup

  1. temperaturecooled to room temperature
  2. extractionAfter extraction with ethyl acetate (3×50 mL)
  3. dry with materialthe organic phase was dried over Na2SO4
  4. concentrationconcentrated
  5. customthe crude was purified by silica-gel column chromatography (ethyl acetate/petroleum ether=1/4)

Sources & evidence

ORD record
ord-1a6374f54f57446f913e4bd5549148e7
Source dataset
uspto-grants-2014_04
Patent number
US08703810B2

Reaction notes

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