3-Chloro-4-fluorobenzaldehyde → (E)-ethyl 3-(3-chloro-4-fluorophenyl)-2-methylacrylate

HRID 514660Notes

Reaction equation

HRID 514660 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[F:10])[CH:5]=O.[C:11]([CH2:16][CH:17]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:13][CH2:14][CH3:15])=[O:12]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4](/[CH:5]=[C:16](\[CH3:17])/[C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:7]=[CH:8][C:9]=1[F:10]

Participants

4

Reactant 2

HCID 5938663-Chloro-4-fluorobenzaldehydeHCID 12607919Ethyl 3-(triphenyl-lambda~5~-phosphanylidene)propanoate

Product 1

HCID 86632358(E)-ethyl 3-(3-chloro-4-fluorophenyl)-2-methylacrylateYield 101.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3-Chloro-4-fluorobenzaldehyde (10 g, 63.1 mmol) was dissolved in 300 mL toluene. (Carboethoxyethylidene)triphenylphosphorane (25 g, 69.4 mmol) was added and the mixture was heated to reflux overnight. The solution was cooled, diluted with hexanes and the solid was filtered. The filtrate was evaporated in vacuo, and the residue was dissolved in ether and filtered through a plug of silica using ether as eluent. The solvent was evaporated in vacuo to afford the title compound (15.55 g) as a semi solid. 1H NMR (300 MHz, CDCl3) δ ppm 7.56 (s, 1H), 7.44 (m, 1H), 7.23-7.32 (m, 1H), 7.16 (m, 1H), 4.28 (q, J=7.12 Hz, 2H), 2.09 (d, J=1.36 Hz, 3H), 1.35 (t, J=7.36 Hz, 3H). MS (DCI+) 243 (M+H).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux overnight
  3. temperatureThe solution was cooled
  4. filtrationthe solid was filtered
  5. customThe filtrate was evaporated in vacuo
  6. dissolutionthe residue was dissolved in ether
  7. filtrationfiltered through a plug of silica
  8. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-8d65b0d21a464d6f9a655bd0675b29de
Source dataset
uspto-grants-2015_08
Patent number
US09108905B2

Reaction notes

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