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

HRID 2167144Notes

Reaction equation

HRID 2167144 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 n-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-6a5dd8398c144a578556394bdfd149f5
Source dataset
uspto-grants-2015_06
Patent number
US09045389B2

Reaction notes

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