2-Chloro-6-fluorobenzaldehyde → 2-Chloro-6-fluorostyrene

HRID 2046635Notes

Reaction equation

HRID 2046635 reaction equation
[CH3:1]C(C)([O-])C.[K+].[Cl:7][C:8]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[C:9]=1[CH:10]=O>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O1CCCC1>[Cl:7][C:8]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[C:9]=1[CH:10]=[CH2:1]

Participants

5

Reactant 2

HCID 678472-Chloro-6-fluorobenzaldehydeHCID 23665647Potassium tert-butoxide

Product 1

HCID 121749902-Chloro-6-fluorostyrene

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent3×

Procedure

Under an argon atmosphere, to a suspension (1.1 L) of methyltriphenylphosphonium bromide (90 g) in dry tetrahydrofuran was added a solution (264 mL) of 1 mol/L-potassium tert-butoxide in tetrahydrofuran with stirring under ice-cooling, and the mixture was stirred at the same temperature for 30 min. Then, a solution (165 mL) of 2-chloro-6-fluorobenzaldehyde (34.5 g) in tetrahydrofuran was added to the mixture, and the mixture was stirred for 30 min. The insoluble material was removed with celite, and the filtrate was concentrated under reduced pressure. Ethyl acetate was added to the residue and, after triturating, the crystals were collected by filtration and concentrated. The residue was purified by silica gel column chromatography (developing solvent: hexane) using NH-silica gel (manufactured by Fuji Silysia Chemical Ltd.) to give the title compound as a colorless oil (yield: 20.7 g).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at the same temperature for 30 min
  3. stirringthe mixture was stirred for 30 min
  4. customThe insoluble material was removed with celite
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. additionEthyl acetate was added to the residue
  7. customafter triturating
  8. filtrationthe crystals were collected by filtration
  9. concentrationconcentrated
  10. customThe residue was purified by silica gel column chromatography (developing solvent: hexane)

Sources & evidence

ORD record
ord-92c37b5dda6d4f05a8cb5cb81ba6289f
Source dataset
uspto-grants-2013_11
Patent number
US08592452B2

Reaction notes

Loading…