Thionyl Chloride → 3-Fluoro-4-(trifluoromethyl)benzyl chloride

HRID 1610301Notes

Reaction equation

HRID 1610301 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[C:10]([F:13])([F:12])[F:11])[CH2:5]O.S(Cl)([Cl:16])=O>C(Cl)(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[C:10]([F:13])([F:12])[F:11])[CH2:5][Cl:16]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 27375623-Fluoro-4-(trifluoromethyl)benzyl alcohol

Product 1

HCID 222620703-Fluoro-4-(trifluoromethyl)benzyl chlorideYield 87%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To absolution of 3-fluoro-4-(trifluoromethyl)benzyl alcohol (10 g, 52 mmol) in chloroform (20 ml) was added thionyl chloride (18.5 ml, 257 mmol) and the mixture was heated under ref lux for 4 hrs. The reaction solution was concentrated. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1) to give 3-fluoro-4-(trifluoromethyl)benzyl chloride (9.52 g, 87%).

Workup

  1. temperaturethe mixture was heated under ref lux for 4 hrs
  2. concentrationThe reaction solution was concentrated
  3. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-bb96693162034c8f9ed3547559716fc4
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

Loading…