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

HRID 910361Notes

Reaction equation

HRID 910361 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 1N 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-e819a27052444d88bf596492b46e2956
Source dataset
uspto-grants-2011_09
Patent number
US08022089B2

Reaction notes

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