Thionyl Chloride → (E)-2-(3-Chloroprop-1-en-1-yl)-1,4-difluorobenzene

HRID 1767140Notes

Reaction equation

HRID 1767140 reaction equation
S(Cl)([Cl:3])=O.N1C2C=CC=CC=2N=N1.[F:14][C:15]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:16]=1[CH:17]=[CH:18][CH2:19]O>ClCCl>[Cl:3][CH2:19]/[CH:18]=[CH:17]/[C:16]1[CH:21]=[C:22]([F:25])[CH:23]=[CH:24][C:15]=1[F:14]

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 534015802,5-Difluorocinnamyl alcoholHCID 178418385HCID 178418385, compound

Product 1

HCID 11608064(E)-2-(3-Chloroprop-1-en-1-yl)-1,4-difluorobenzeneYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 0.34 cm3 (4.66 mmol) of thionyl chloride and 0.555 g (4.66 mmol) of benzotriazole in 40 cm3 of dichloromethane is added at a temperature in the region of 20° C. under an argon atmosphere to 0.646 g (3.8 mmol) of 2,5-difluorocinnamyl alcohol in solution in 40 cm3 of dichloromethane. After stirring for 10 minutes, the reaction mixture is filtered on No. 3 sintered glass and the solid residue rinsed with twice 10 cm3 of dichloromethane. The filtrate is washed 3 times with 30 cm3 of water. The organic phase is dried over magnesium sulfate and filtered to give a solution of 2-[(1E)-3-chloro-1-propenyl]-1,4-difluorobenzene (3.8 mmol) which is then concentrated to dryness under reduced pressure (2.7 kPa) at a temperature in the region of 20° C., before dissolution in acetonitrile.

Workup

  1. filtrationthe reaction mixture is filtered on No
  2. wash3 sintered glass and the solid residue rinsed with twice 10 cm3 of dichloromethane
  3. washThe filtrate is washed 3 times with 30 cm3 of water
  4. dry with materialThe organic phase is dried over magnesium sulfate
  5. filtrationfiltered

Sources & evidence

ORD record
ord-1c690237919a464298268cc1a552fd28
Source dataset
uspto-grants-2007_06
Patent number
US07232833B2

Reaction notes

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