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

HRID 405256

Reaction equation

HRID 405256 reaction equation
[Li+].CC([N-]C(C)C)C.[Cl:9][C:10]1[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:13]=[C:12]([O:20][CH2:21][O:22][CH3:23])[CH:11]=1.CN([CH:27]=[O:28])C>C1COCC1>[Cl:9][C:10]1[CH:15]=[C:14]([C:16]([F:18])([F:19])[F:17])[CH:13]=[C:12]([O:20][CH2:21][O:22][CH3:23])[C:11]=1[CH:27]=[O:28]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 2724682Lithium diisopropylamideHCID 866742861-Chloro-3-(methoxymethoxy)-5-(trifluoromethyl)benzene

Product 1

HCID 866742872-Chloro-6-(methoxymethoxy)-4-(trifluoromethyl)benzaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A 1.6M LDA solution (12.6 mL, 20.1 mmol) was added to a −78° C. THF solution (50 mL) of 1-chloro-3-(methoxymethoxy)-5-(trifluoromethyl)benzene (from above). After 30 min neat DMF (3.9 mL, 50.0 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-18cdfcacb0de4a1bac2fe48d611cf668
Source dataset
uspto-grants-2014_06
Patent number
US08748624B2

Linked notes

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