Methyltriphenylphosphonium iodide → 1,2-Bis(difluoromethoxy)-4-vinylbenzene

HRID 1992347Notes

Reaction equation

HRID 1992347 reaction equation
[CH3:1]C(C)([O-])C.[K+].[I-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[F:28][CH:29]([F:43])[O:30][C:31]1[CH:32]=[C:33]([CH:36]=[CH:37][C:38]=1[O:39][CH:40]([F:42])[F:41])[CH:34]=O>C1COCC1>[F:41][CH:40]([F:42])[O:39][C:38]1[CH:37]=[CH:36][C:33]([CH:34]=[CH2:1])=[CH:32][C:31]=1[O:30][CH:29]([F:43])[F:28]

Participants

5

Reactant 3

HCID 638159Methyltriphenylphosphonium iodideHCID 145092693,4-Bis(difluoromethoxy)benzaldehydeHCID 23665647Potassium tert-butoxide

Product 1

HCID 685199461,2-Bis(difluoromethoxy)-4-vinylbenzene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Potassium tert-butoxide (6.7 g, 0.0683 mol) was taken in dry THF (25 mL) and stirred at 0° C. under a nitrogen atmosphere for 15 min. Methyl triphenylphosphonium iodide (27.6 g, 0.0683 mol; see step (ii) above) was then added, followed by 3,4-bis(difluoromethoxy)benzaldehyde (8 g, 0.034 mol; see step (i) above). The reaction mixture was then stirred for 1 h at RT, before being quenched with water. The organic solvents were evaporated under reduced pressure and the aqueous layer extracted with dichloromethane. Evaporation of the solvents followed, by chromatography of the residue over silica gel (using petroleum ether in ethyl acetate as eluent) afforded the sub-title compound as a pale yellow liquid. Yield: 6.5 g

Workup

  1. stirringThe reaction mixture was then stirred for 1 h at RT
  2. custombefore being quenched with water
  3. customThe organic solvents were evaporated under reduced pressure
  4. extractionthe aqueous layer extracted with dichloromethane
  5. customEvaporation of the solvents

Sources & evidence

ORD record
ord-5659e3aad312417791223a22e8bd8b96
Source dataset
uspto-grants-2010_01
Patent number
US07648985B2

Reaction notes

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