Thionyl Chloride → 5-Chloromethyl-4-trifluoromethyl-2-(4-trifluoromethyl-phenyl)-pyrimidine

HRID 1242441Notes

Reaction equation

HRID 1242441 reaction equation
[F:1][C:2]([F:22])([F:21])[C:3]1[C:8]([CH2:9]O)=[CH:7][N:6]=[C:5]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)[N:4]=1.S(Cl)([Cl:25])=O>ClCCl>[Cl:25][CH2:9][C:8]1[C:3]([C:2]([F:22])([F:21])[F:1])=[N:4][C:5]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 21935616[4-Trifluoromethyl-2-(4-trifluoromethyl-phenyl)-pyrimidin-5-yl]-methanol

Product 1

HCID 219357875-Chloromethyl-4-trifluoromethyl-2-(4-trifluoromethyl-phenyl)-pyrimidineYield 90.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A cooled (0° C.) solution of 0.081 g (0.25 mmol) of [4-trifluoromethyl-2-(4-trifluoromethyl-phenyl)-pyrimidin-5-yl]-methanol in 2.5 ml dichloromethane was treated with 0.04 ml (0.50 mmol) thionylchloride and stirred for 14 h at RT. The reaction was evaporated, dissolved in ether and twice in heptane and evaporated to give 0.077 g of pure 5-chloromethyl-4-trifluoromethyl-2-(4-trifluoromethyl-phenyl)-pyrimidine.

Workup

  1. customThe reaction was evaporated
  2. dissolutiondissolved in ether and twice in heptane
  3. customevaporated

Sources & evidence

ORD record
ord-4af7533276dd434aa6f9a7d5ab5fc28e
Source dataset
uspto-grants-2006_10
Patent number
US07115611B2

Reaction notes

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