Thionyl Chloride → 1-(Chloromethyl)-4-(4-(trifluoromethyl)phenoxy)benzene

HRID 604456Notes

Reaction equation

HRID 604456 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]1[CH:17]=[CH:16][C:6]([O:7][C:8]2[CH:13]=[CH:12][C:11]([CH2:14]O)=[CH:10][CH:9]=2)=[CH:5][CH:4]=1.S(Cl)([Cl:22])=O.N1C2C=CC=CC=2N=N1>ClCCl>[Cl:22][CH2:14][C:11]1[CH:12]=[CH:13][C:8]([O:7][C:6]2[CH:16]=[CH:17][C:3]([C:2]([F:19])([F:18])[F:1])=[CH:4][CH:5]=2)=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 57543181(4-(4-(Trifluoromethyl)phenoxy)phenyl)methanolHCID 178418385HCID 178418385, compound

Product 1

HCID 146742921-(Chloromethyl)-4-(4-(trifluoromethyl)phenoxy)benzene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5.37 g 1H-Benzotriazole were dissolved in 10.9 ml thionyl chloride. The solution was diluted with dichloromethane to a total volume of 100 ml to obtain a 1.5 M solution of thionylchloride and 1H-Benzotriazole. 600 mg [4-(4-Trifluoromethyl-phenoxy)-phenyl]-methanol were dissolved in 50 ml dichloromethane. 1.86 ml of the above 1.5 M solution of thionylchloride and 1H-Benzotriazole were added. The reaction mixture was stirred at room temperature for three hours. The precipitate was filtered off through a pad of Na2SO4. The filtrate was evaporated in vacuo and the residue purified by flash chromatography on silica gel with the eluents n-heptane:ethyl acetate=1:2=>1:1 to obtain 613 mg 1-Chloromethyl-4-(4-Trifluoromethyl-phenoxy)-benzene.

Workup

  1. filtrationThe precipitate was filtered off through a pad of Na2SO4
  2. customThe filtrate was evaporated in vacuo
  3. customthe residue purified by flash chromatography on silica gel with the eluents n-heptane

Sources & evidence

ORD record
ord-59ddff05f78646f28e2d0e1ca2a4f6ac
Source dataset
uspto-grants-2011_03
Patent number
US07910612B2

Reaction notes

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