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

HRID 1767133Notes

Reaction equation

HRID 1767133 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 0.66 cm3 (9.07 mmol) of thionyl chloride and 1.08 g (9.07 mmol) of benzotriazole in 70 cm3 of dichloromethane are added at a temperature in the region of 20° C., under an argon atmosphere, to 1.25 g (7.34 mmol) of 2,5-difluorocinnamyl alcohol in solution in 130 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 20 cm3 of dichloromethane. The filtrate is washed with 3 times 75 cm3 of water. The organic phase is dried over anhydrous magnesium sulfate and filtered to give a solution of 2-[(1E)-3-chloro-1-propenyl]-1,4-difluorobenzene (7.34 mmol) which is immediately used as it is in the next step.

Workup

  1. filtrationthe reaction mixture is filtered on No
  2. wash3 sintered glass and the solid residue rinsed with twice 20 cm3 of dichloromethane
  3. washThe filtrate is washed with 3 times 75 cm3 of water
  4. dry with materialThe organic phase is dried over anhydrous magnesium sulfate
  5. filtrationfiltered

Sources & evidence

ORD record
ord-8b311139721941669c8673fb1b52d995
Source dataset
uspto-grants-2007_06
Patent number
US07232833B2

Reaction notes

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