Thionyl Chloride → 1-Chloro-4-(chloromethyl)-2-(trifluoromethyl)benzene

HRID 2274049Notes

Reaction equation

HRID 2274049 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]O)=[CH:4][C:3]=1[C:10]([F:13])([F:12])[F:11].S(Cl)([Cl:16])=O>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][Cl:16])=[CH:4][C:3]=1[C:10]([F:13])([F:12])[F:11]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 27781114-Chloro-3-(trifluoromethyl)benzyl alcohol

Product 1

HCID 130942621-Chloro-4-(chloromethyl)-2-(trifluoromethyl)benzeneYield 97.5%

Conditions

Temperature
50 °C

Procedure

(4-Chloro-3-(trifluoromethyl)phenyl)methanol (5.1 g, 24.22 mmol) was added in small portions to thionyl chloride (20 mL, 275 mmol). The reaction mixture was stirred at 50° C. for 18 h and heated under reflux for 23 h. The mixture was concentrated and dried under high vacuum to give the title compound as a colorless liquid (5.41 g). 1H NMR (400 MHz, CDCl3) δ ppm 4.58 (s, 2H), 7.50-7.51 (m, 2H), 7.71 (s, 1H).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 23 h
  3. concentrationThe mixture was concentrated
  4. customdried under high vacuum

Sources & evidence

ORD record
ord-f7fc112ccc724195a9dfd0a3167ff91b
Source dataset
uspto-grants-2015_09
Patent number
US09126932B2

Reaction notes

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