Thionyl Chloride → 4-Chloro-1-(chloromethyl)-2-fluorobenzene

HRID 1870786Notes

Reaction equation

HRID 1870786 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6]O)=[C:4]([F:10])[CH:3]=1.S(Cl)([Cl:13])=O>O1CCCC1.N1C=CC=CC=1>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][Cl:13])=[C:4]([F:10])[CH:3]=1

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 2773609(4-Chloro-2-fluorophenyl)methanol

Product 1

HCID 148779334-Chloro-1-(chloromethyl)-2-fluorobenzene

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent

Procedure

Then, 16.5 g of 4-chloro-2-fluorobenzylalcohol was dissolved in 150 ml of tetrahydrofuran and 1 ml of pyridine, to which 10 ml of thionyl chloride was added dropwise at 5° C., and the mixture was stirred for 2.5/6 hours. After cormpletion of the reaction, the reaction mixture was concentrated, and the precipitated crystals were collected by filtration. The filtrate was subjected to silica gel column chromatography, which afforded 18.5 g of 4-chloro-2-fluorobenzyl chloride.

Workup

  1. custom5/6 hours
  2. customAfter cormpletion of the reaction
  3. concentrationthe reaction mixture was concentrated
  4. filtrationthe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-1a1c681692594825969273d9bd98fa08
Source dataset
uspto-grants-2000_08
Patent number
US06100257

Reaction notes

Loading…