Ethyl Acetate → Methyl 3-nitro-5-(trifluoromethyl)benzoate

HRID 2200136Notes

Reaction equation

HRID 2200136 reaction equation
S(Cl)(Cl)=O.[N+:5]([C:8]1[CH:9]=[C:10]([CH:14]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:16]=1)[C:11]([OH:13])=[O:12])([O-:7])=[O:6].[CH3:21]COC(C)=O>CO>[N+:5]([C:8]1[CH:9]=[C:10]([CH:14]=[C:15]([C:17]([F:18])([F:19])[F:20])[CH:16]=1)[C:11]([O:13][CH3:21])=[O:12])([O-:7])=[O:6]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 24386Thionyl ChlorideHCID 6166023-Nitro-5-(trifluoromethyl)benzoic acid

Product 1

HCID 18942157Methyl 3-nitro-5-(trifluoromethyl)benzoateYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Add thionyl chloride (2 mL) dropwise to the solution of 3-nitro-5-(trifluoromethyl)benzoic acid (1.5 g, 6.4 mmol) in methanol (20 mL), reflux for 5 hrs. TLC (PE:EtOAc=1:1) shows the reaction is complete. Concentrate under reduced pressure to give the crude product (1.8 g, 100%) which is used in next step without further purification.

Workup

  1. temperaturereflux for 5 hrs
  2. concentrationConcentrate under reduced pressure

Sources & evidence

ORD record
ord-257422235d964f9abf47e5d1eb569a7b
Source dataset
uspto-grants-2016_06
Patent number
US09359338B2

Reaction notes

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