Thionyl Chloride → 1-Allyloxy-3-fluoro-4-chloromethyl-benzene

HRID 2113890Notes

Reaction equation

HRID 2113890 reaction equation
[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11]O)=[C:7]([F:13])[CH:6]=1)[CH:2]=[CH2:3].S(Cl)([Cl:16])=O>ClCCl.CN(C=O)C>[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][Cl:16])=[C:7]([F:13])[CH:6]=1)[CH:2]=[CH2:3]

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 69292836(4-Allyloxy-2-fluoro-phenyl)-methanol

Product 1

HCID 692933781-Allyloxy-3-fluoro-4-chloromethyl-benzeneYield 97%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 4.20 g (23.1 mmol) (4-allyloxy-2-fluoro-phenyl)-methanol in 80 ml dichloro-methane and 0.5 ml DMF was cooled to 0° C. 2.17 ml (3.57 g, 30.0 mmol) thionyl chloride were added slowly and then stirred for 1 h at room temperature. Dichloromethane was distilled off. The residue was taken up in 100 ml ethyl acetate and washed with concentrated sodium carbonate solution. The organic phase was dried and evaporated to give 4.47 g (97%) 1-allyloxy-3-fluoro-4-chloromethyl-benzene as colored oil.

Workup

  1. distillationDichloromethane was distilled off
  2. washwashed with concentrated sodium carbonate solution
  3. customThe organic phase was dried
  4. customevaporated

Sources & evidence

ORD record
ord-3e1914b6e5b347aab30dda1f8f095043
Source dataset
uspto-grants-2008_10
Patent number
US07432291B2

Reaction notes

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