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Toluene → 4-Benzyloxy-3-trifluoromethylbenzoyl chloride

HRID 385115
Notes
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Reaction equation

HRID 385115 reaction equation
[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13](O)=[O:14])=[CH:11][C:10]=1[C:18]([F:21])([F:20])[F:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C)C=CC=CC=1.S(Cl)([Cl:31])=O>CN(C)C=O>[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([Cl:31])=[O:14])=[CH:11][C:10]=1[C:18]([F:21])([F:20])[F:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 1140TolueneHCID 24386Thionyl ChlorideHCID 167490234-(Benzyloxy)-3-(trifluoromethyl)benzoic acid

Product 1

HCID 866681754-Benzyloxy-3-trifluoromethylbenzoyl chloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To 4-benzyloxy-3-trifluoromethylbenzoic acid (444 mg), toluene (5 mL), N,N-dimethylformamide (2 droplets) and thionyl chloride (0.16 mL) were added, and then the mixture was stirred at 60° C. for 20 hours. The solvent was distilled off under reduced pressure and then azeotroped with toluene, and the obtained product was used for the synthesis of (h).

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. customazeotroped with toluene
  3. customthe obtained product was used for the synthesis of (h)

Sources & evidence

ORD record
ord-f0f8665d587f4bf0a4796929d3797997
Source dataset
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08367843B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes