Thionyl Chloride → 4-(Chloromethyl)phenyl 4-chloro-3-(trifluoromethyl)phenyl ether

HRID 474607Notes

Reaction equation

HRID 474607 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15]O)=[CH:11][CH:10]=2)=[CH:4][C:3]=1[C:17]([F:20])([F:19])[F:18].S(Cl)([Cl:23])=O>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][Cl:23])=[CH:11][CH:10]=2)=[CH:4][C:3]=1[C:17]([F:20])([F:19])[F:18]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 66825563(4-(4-Chloro-3-(trifluoromethyl)phenoxy)phenyl)methanol

Product 1

HCID 668255374-(Chloromethyl)phenyl 4-chloro-3-(trifluoromethyl)phenyl etherYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the solution of (4-{[4-chloro-3-(trifluoromethyl)phenyl]oxy}phenyl)methanol (3 g, 9.91 mmol) in DCM (90 mL), was added thionyl chloride (7.5 mL, 103 mmol) dropwise. The mixture was stirred at room temperature for 1.5 h. After removing the solvent, the residue was dissolved in DCM, then washed with water twice, dried over Na2SO4. Concentration in vacuo afforded the title compound (2.8 g, 88% yield) as light brown oil. LCMS: rt=4.14 min

Workup

  1. customAfter removing the solvent
  2. dissolutionthe residue was dissolved in DCM
  3. washwashed with water twice
  4. dry with materialdried over Na2SO4
  5. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-84ac9d06051e483b9489580f834e55c7
Source dataset
uspto-grants-2014_01
Patent number
US08637536B2

Reaction notes

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