Thionyl Chloride → 2-Chloromethyl-1-cyclopropyl-3-fluorobenzene

HRID 1190929Notes

Reaction equation

HRID 1190929 reaction equation
[CH:1]1([C:4]2[CH:9]=[CH:8][CH:7]=[C:6]([F:10])[C:5]=2[CH2:11]O)[CH2:3][CH2:2]1.S(Cl)([Cl:15])=O>ClCCl>[Cl:15][CH2:11][C:5]1[C:6]([F:10])=[CH:7][CH:8]=[CH:9][C:4]=1[CH:1]1[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 66652970(2-Cyclopropyl-6-fluorophenyl)-methanol

Product 1

HCID 679971832-Chloromethyl-1-cyclopropyl-3-fluorobenzeneYield 54.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(2-Cyclopropyl-6-fluorophenyl)-methanol (4, 5.56 g, 34 mmol) was dissolved in dichloromethane (100 mL) and thionyl chloride (2.49 mL, 34 mmol) was added. The mixture was refluxed for 4 h and evaporated. The crude product was purified by column chromatography over silica, eluting with n-hexane:ethyl acetate (95:5). The title compound (3.41 g, 18.4 mmol, 54%) was isolated as a pale yellow oil.

Workup

  1. temperatureThe mixture was refluxed for 4 h
  2. customevaporated
  3. customThe crude product was purified by column chromatography over silica
  4. washeluting with n-hexane:ethyl acetate (95:5)

Sources & evidence

ORD record
ord-d7dfc1ee2f344b5ebcf1e8993f90f0af
Source dataset
uspto-grants-2014_03
Patent number
US08680099B2

Reaction notes

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