Sulfuric Acid → 2-Chloro-3-(trifluoromethyl)benzaldehyde

HRID 1789034Notes

Reaction equation

HRID 1789034 reaction equation
C([Li])CCC.[Cl:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13]([F:16])([F:15])[F:14].CN(C1C=CC=CC=1)[CH:19]=[O:20].S(=O)(=O)(O)O>O1CCCC1>[Cl:6][C:7]1[C:8]([C:13]([F:14])([F:15])[F:16])=[CH:9][CH:10]=[CH:11][C:12]=1[CH:19]=[O:20]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 69211-Chloro-2-(trifluoromethyl)benzeneHCID 66737N-MethylformanilideHCID 178418339Butyllithium

Product 1

HCID 27366722-Chloro-3-(trifluoromethyl)benzaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Butyl lithium (36.4 ml of 1.6M in hexane) was added to a stirred solution at -65° of 1-chloro-2-(trifluoromethyl)-benzene (10 g) in dry tetrahydrofuran (100 ml) over 20 mins. After stirring for 1.5 hours at -65°, a solution of N-methyl-N-phenylformamide (6.85 ml) in tetrahydrofuran (30 ml) was added over 1 hour. The reaction mixture was left at this temperature for 1.5 hours and then allowed to reach room temperature. It was then poured onto 10% sulphuric acid, extracted with ether and the organic extract was washed with brine, dried (Na2SO4) and the solvent removed in vacuo. The residue was distilled (20 mmHg, oven temperature 100°-125°); the distillate was cooled, filtered and the solid washed with petroleum ether (60°-80°) to give the desired aldehyde (3.5 g) as a colourless solid.

Workup

  1. waitThe reaction mixture was left at this temperature for 1.5 hours
  2. customto reach room temperature
  3. extractionextracted with ether
  4. extractionthe organic extract
  5. washwas washed with brine
  6. dry with materialdried (Na2SO4)
  7. customthe solvent removed in vacuo
  8. distillationThe residue was distilled (20 mmHg, oven temperature 100°-125°)
  9. temperaturethe distillate was cooled
  10. filtrationfiltered
  11. washthe solid washed with petroleum ether (60°-80°)

Sources & evidence

ORD record
ord-1ff3c7bf1efc4f8b9c752f5d2e231c42
Source dataset
uspto-grants-1987_08
Patent number
US04686217

Reaction notes

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