3-Fluoro-p-anisaldehyde → Ethyl (E)-3-(3-Fluoro-4-methoxyphenyl)acrylate

HRID 445814Notes

Reaction equation

HRID 445814 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH:5]=O.[C:12]([CH:17]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:14][CH2:15][CH3:16])=[O:13]>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4](/[CH:5]=[CH:17]/[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:7]=[CH:8][C:9]=1[O:10][CH3:11]

Participants

4

Reactant 2

HCID 676963-Fluoro-p-anisaldehydeHCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester

Product 1

HCID 12330260Ethyl (E)-3-(3-Fluoro-4-methoxyphenyl)acrylateYield 87.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

The mixture of 3-fluoro-4-methoxybenzaldehyde (5.1 g, 33.0 mmol) and (carbethoxymethylene)triphenylphosphorane (17.2 g, 49.5 mmol) in anhydrous toluene (165 mL) was refluxed at 120° C. under nitrogen for 4 hours. The solvent was removed in vacuo and purified by silica gel chromatography (10-20% EtOAc in hexanes) to provide (E)-ethyl 3-(3-fluoro-4-methoxyphenyl)acrylate (537) (6.5 g, 87.6%) as a white solid.

Workup

  1. customThe solvent was removed in vacuo
  2. custompurified by silica gel chromatography (10-20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-0aa79464051f46038d0ba8f089f66f32
Source dataset
uspto-grants-2013_07
Patent number
US08476308B2

Reaction notes

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