4-Fluoro-3,5-dimethylbenzaldehyde → Ethyl 3-(4-fluoro-3,5-dimethylphenyl)-2-methylacrylate

HRID 1158126Notes

Reaction equation

HRID 1158126 reaction equation
[CH2:1]([O:3][C:4]([CH2:6][CH2:7]P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:5])[CH3:2].[CH3:27][C:28]1[CH:29]=[C:30]([CH:33]=[C:34]([CH3:37])[C:35]=1[F:36])[CH:31]=O>C1COCC1>[F:36][C:35]1[C:28]([CH3:27])=[CH:29][C:30]([CH:31]=[C:6]([CH3:7])[C:4]([O:3][CH2:1][CH3:2])=[O:5])=[CH:33][C:34]=1[CH3:37]

Participants

4

Reactant 2

HCID 120407104-Fluoro-3,5-dimethylbenzaldehydeHCID 178472276HCID 178472276, compound

Product 1

HCID 68642179Ethyl 3-(4-fluoro-3,5-dimethylphenyl)-2-methylacrylateYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

Ethoxy-carbonylethylene triphenyl phosphorane (0.476 g, 1.314 mmol) and 3,5-dimethyl-4-fluorobenzaldehyde (0.200 g, 1.314 mmol) were weighed into a microwave tube followed by the addition of 3 mL of THF. After stirred under microwave irradiation at 100° C. for 1 h, the reaction mixture was concentrated under reduced pressure. The product was isolated by Flash column chromatography (silica gel column) eluting with 0-30% ethyl acetate/hexanes to give the title compound as a white solid (0.267 g, 86% yield). LC-MS: tR=10.6 & 11.3 min; m/z 237 (M+H)+.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. customThe product was isolated by Flash column chromatography (silica gel column)
  3. washeluting with 0-30% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-4b35825cf46e4ecd8c1b6e22d95557c9
Source dataset
uspto-grants-2010_10
Patent number
US07807720B2

Reaction notes

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