Thionyl Chloride → 4-(Trifluoromethoxy)phenoxyacetyl chloride

HRID 1009193Notes

Reaction equation

HRID 1009193 reaction equation
[F:1][C:2]([F:16])([F:15])[O:3][C:4]1[CH:14]=[CH:13][C:7]([O:8][CH2:9][C:10](O)=[O:11])=[CH:6][CH:5]=1.S(Cl)([Cl:19])=O>CN(C=O)C>[F:1][C:2]([F:16])([F:15])[O:3][C:4]1[CH:14]=[CH:13][C:7]([O:8][CH2:9][C:10]([Cl:19])=[O:11])=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 6977052-(4-(Trifluoromethoxy)phenoxy)acetic acid

Product 1

HCID 27773084-(Trifluoromethoxy)phenoxyacetyl chloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Procedure

(4-Trifluoromethoxyphenoxy)-acetic acid (20.7 g, 88 mmol) was dissolved in thionyl chloride (100 mL). DMF (3 drops) was added to the solution. The solution was stirred for 14 hours. The thionyl chloride was removed in vacuo. The resulting oil was dissolved in dichloromethane, filtered through sodium sulfate and concentrate in vacuo to afford the title compound as a paste-like solid (21.8 g, 97% from the phenol): MS (EI-GCMS) for C9H6ClF3O3: 254 (M+).

Workup

  1. customThe thionyl chloride was removed in vacuo
  2. dissolutionThe resulting oil was dissolved in dichloromethane
  3. filtrationfiltered through sodium sulfate
  4. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-008a93ab7eb44053911af6dbbb4c8df6
Source dataset
uspto-grants-2011_07
Patent number
US07973061B2

Reaction notes

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