Hydrochloric Acid → 4-formyl-2-methyl-N-(2,2,2-trifluoroethyl)benzoic acid amide

HRID 1444878Notes

Reaction equation

HRID 1444878 reaction equation
Br[C:2]1[CH:15]=[CH:14][C:5]([C:6]([NH:8][CH2:9][C:10]([F:13])([F:12])[F:11])=[O:7])=[C:4]([CH3:16])[CH:3]=1.C([Li])CCC.CN(C)[CH:24]=[O:25].Cl>O1CCCC1.O>[CH:24]([C:2]1[CH:15]=[CH:14][C:5]([C:6]([NH:8][CH2:9][C:10]([F:13])([F:12])[F:11])=[O:7])=[C:4]([CH3:16])[CH:3]=1)=[O:25]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 667843104-Bromo-2-methyl-N-(2,2,2-trifluoro-ethyl)-benzamideHCID 178418339Butyllithium

Product 1

HCID 866114664-formyl-2-methyl-N-(2,2,2-trifluoroethyl)benzoic acid amide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

In a solution of 1.00 g of 4-bromo-2-methyl-N-(2,2,2-trifluoroethyl)benzoic acid amide in 15 ml of tetrahydrofuran under nitrogen atmosphere, 4.7 ml of n-butyl lithium (1.58M hexane solution) was added dropwise at −70° C. with stirring, and then 0.4 ml of N,N-dimethylformamide were added dropwise. After stirring at the same temperature for 30 minutes, 10 ml of 1 N hydrochloric acid and then 30 ml of water were added, and extracted with ethyl acetate (30 ml×2). The organic phase was dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure to obtain 0.80 g of the aimed product as pale yellow crystal.

Workup

  1. stirringAfter stirring at the same temperature for 30 minutes
  2. extractionextracted with ethyl acetate (30 ml×2)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-9784a0b4d469490a9e07f8b72c0473f9
Source dataset
uspto-grants-2010_02
Patent number
US07662972B2

Reaction notes

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