o-Fluorobenzaldehyde → (E)-ethyl 3-(2-fluorophenyl)-2-methylacrylate

HRID 514658Notes

Reaction equation

HRID 514658 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[C:10]([CH2:15][CH:16]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:12][CH2:13][CH3:14])=[O:11]>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1/[CH:4]=[C:15](\[CH3:16])/[C:10]([O:12][CH2:13][CH3:14])=[O:11]

Participants

4

Reactant 2

HCID 67970o-FluorobenzaldehydeHCID 12607919Ethyl 3-(triphenyl-lambda~5~-phosphanylidene)propanoate

Product 1

HCID 86632357(E)-ethyl 3-(2-fluorophenyl)-2-methylacrylateYield 126%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-Fluorobenzaldehyde (5.0 g, 40.3 mmol) was dissolved in 150 mL toluene. (Carboethoxyethylidene)triphenylphosphorane (42 g; 116 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, then dissolved in ether and filtered through a plug of silica gel using ether as eluent. The solvents were evaporated in vacuo to afford the title compound (10.57 g) as a yellow solid. 1H NMR (300 MHz, CDCl3) δ ppm 7.70 (s, 1H), 7.26-7.38 (m, 3H), 7.17 (m, 2H), 4.28 (q, J=7.12 Hz, 2H), 2.04 (s, 3H), 1.35 (t, J=7.12 Hz, 3H).

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. dissolutiondissolved in ether
  7. filtrationfiltered through a plug of silica gel
  8. customThe solvents were evaporated in vacuo

Sources & evidence

ORD record
ord-f4119feedcc4419c9ef41bf244ac39c9
Source dataset
uspto-grants-2015_08
Patent number
US09108905B2

Reaction notes

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