Dimethylformamide → 2-Chloro-6-methoxy-4-(trifluoromethyl)benzaldehyde

HRID 405244Notes

Reaction equation

HRID 405244 reaction equation
[Li]CCCC.[Cl:6][C:7]1[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=[C:9]([O:17][CH3:18])[CH:8]=1.CN([CH:22]=[O:23])C>C1COCC1>[Cl:6][C:7]1[CH:12]=[C:11]([C:13]([F:15])([F:16])[F:14])[CH:10]=[C:9]([O:17][CH3:18])[C:8]=1[CH:22]=[O:23]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 38491413-Chloro-5-(trifluoromethyl)anisoleHCID 178418339Butyllithium

Product 1

HCID 840702922-Chloro-6-methoxy-4-(trifluoromethyl)benzaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A 2M BuLi solution (2.07 mL, 4.3 mmol) was added to a −78° C. THF solution (20 mL) of 1-chloro-3-methoxy-5-(trifluoromethyl)benzene (870 mg, 4.1 mmol). After 45 min neat DMF (0.39 mL, 5.0 mmol) was added, and the resulting solution was allowed to warm to 0° C. gradually, quenched with NH4Cl solution, and extracted with diethyl ether. The combined extracts were dried (Na2SO4), concentrated, and purified via column chromatography to yield the title compound.

Workup

  1. customquenched with NH4Cl solution
  2. extractionextracted with diethyl ether
  3. dry with materialThe combined extracts were dried (Na2SO4)
  4. concentrationconcentrated
  5. custompurified via column chromatography

Sources & evidence

ORD record
ord-4e10055de67045dc872e28b49a26438e
Source dataset
uspto-grants-2014_06
Patent number
US08748624B2

Reaction notes

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