Water → 2-Chloro-3-(trifluoromethyl)benzaldehyde

HRID 1494588Notes

Reaction equation

HRID 1494588 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([F:11])([F:10])[F:9].C([Li])CCC.CN(C)[CH:19]=[O:20].O>O1CCCC1.CCCCCC>[Cl:1][C:2]1[C:3]([C:8]([F:9])([F:10])[F:11])=[CH:4][CH:5]=[CH:6][C:7]=1[CH:19]=[O:20]

Participants

7

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 69211-Chloro-2-(trifluoromethyl)benzeneHCID 178418339Butyllithium

Product 1

HCID 27366722-Chloro-3-(trifluoromethyl)benzaldehyde

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

A solution of 0.6 mole of 2-chlorotrifluoromethylbenzene in 1 l of tetrahydrofuran is cooled to -65° C. and 0.58 mole of butyllithium dissolved in hexane is added. The mixture is maintained at the same temperature for 2 hours and a mixture containing 44 ml of dimethylformamide and 200 ml of tetrahydrofuran is then added dropwise. The reaction medium is allowed to return to ambient temperature, 600 ml of water are added, extraction is then carried out with ethyl ether followed by evaporation to dryness. The product is distilled to purify.

Workup

  1. additionis added
  2. temperatureThe mixture is maintained at the same temperature for 2 hours
  3. additionis then added dropwise
  4. customto return to ambient temperature
  5. extractionextraction
  6. customfollowed by evaporation to dryness
  7. distillationThe product is distilled
  8. customto purify

Sources & evidence

ORD record
ord-1614159ade804cd78bcf1e2671810759
Source dataset
uspto-grants-1991_06
Patent number
US05026863

Reaction notes

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