Thionyl Chloride → 5-(Chloromethyl)-{[3-(trifluoromethyl)phenyl]oxy}benzonitrile

HRID 474624Notes

Reaction equation

HRID 474624 reaction equation
O[CH2:2][C:3]1[CH:4]=[CH:5][C:6]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=2)=[C:7]([CH:10]=1)[C:8]#[N:9].S(Cl)([Cl:24])=O>C(Cl)Cl>[Cl:24][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=2)=[C:7]([CH:10]=1)[C:8]#[N:9]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 668254365-(Hydroxymethyl)-2-(3-(trifluoromethyl)phenoxy)benzonitrile

Product 1

HCID 668253585-(Chloromethyl)-{[3-(trifluoromethyl)phenyl]oxy}benzonitrileYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 5-(hydroxymethyl)-2-{[3-(trifluoromethyl)phenyl]oxy}benzonitrile (250 mg, 0.853 mmol) in DCM (4 mL) was added thionyl chloride (0.124 mL, 1.705 mmol) dropwise under nitrogen. The mixture was stirred at room temperature for 2 h. The reaction was quenched with water, adjusted pH about 7 and extracted with DCM. The organic layer was separated and concentrated to afford the title compound (250 mg, 0.802 mmol, 94% yield).

Workup

  1. customThe reaction was quenched with water, adjusted pH about 7
  2. extractionextracted with DCM
  3. customThe organic layer was separated
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-7a6421da9740476d9b11ebe841d0a34a
Source dataset
uspto-grants-2014_01
Patent number
US08637536B2

Reaction notes

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