Dimethylformamide → 2,6-Dichloro-4-(trifluoromethyl)benzaldehyde

HRID 1950917Notes

Reaction equation

HRID 1950917 reaction equation
Br[C:2]1[C:7]([Cl:8])=[CH:6][C:5]([C:9]([F:12])([F:11])[F:10])=[CH:4][C:3]=1[Cl:13].C([Mg]Br)(C)C.CN(C)[CH:21]=[O:22]>O1CCCC1>[Cl:13][C:3]1[CH:4]=[C:5]([C:9]([F:12])([F:11])[F:10])[CH:6]=[C:7]([Cl:8])[C:2]=1[CH:21]=[O:22]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 12682564-Bromo-3,5-dichlorobenzotrifluorideHCID 178418365HCID 178418365, compound

Product 1

HCID 147939142,6-Dichloro-4-(trifluoromethyl)benzaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-10 °C

Procedure

A solution of 4-bromo-3,5-dichlorobenzotrifluoride (1 g, 3.4 mmol) in 1.2 mL tetrahydrofurane was slowly added to isopropylmagnesium bromide (15% in THF, 3.3 g, 3.4 mmol) at max. −10° C. After complete addition the reaction mixture was stirred for 30 min at −10° C. Dimethylformamide (0.275 g, 3.7 mmol) was added and the mixture was slowly warmed up. The mixture was quenched with saturated ammonium chloride solution and extracted three times with ethyl acetate. The combined organic phases were dried on sodium sulfate, filtered and evaporated. The crude product was used without any further purification, brown oil (741 mg, 89%).

Workup

  1. custom−10° C
  2. additionAfter complete addition the reaction mixture
  3. temperaturethe mixture was slowly warmed up
  4. customThe mixture was quenched with saturated ammonium chloride solution
  5. extractionextracted three times with ethyl acetate
  6. customThe combined organic phases were dried on sodium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customThe crude product was used without any further purification, brown oil (741 mg, 89%)

Sources & evidence

ORD record
ord-f142dd022bac44b987dcf826db7a67db
Source dataset
uspto-grants-2013_03
Patent number
US08404673B2

Reaction notes

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