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

HRID 2167149
Notes
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Reaction equation

HRID 2167149 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]([Cl:17])[CH:8]=1.CN([CH:21]=[O:22])C>C1COCC1>[Cl:6][C:7]1[CH:12]=[C:11]([C:13]([F:14])([F:15])[F:16])[CH:10]=[C:9]([Cl:17])[C:8]=1[CH:21]=[O:22]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 353611,3-Dichloro-5-(trifluoromethyl)benzeneHCID 178418339Butyllithium

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A 2M n-BuLi solution (5.8 mL, 11.6 mmol) was added to a −78° C. THF solution (60 mL) of 1,3-dichloro-5-(trifluoromethyl)benzene (2.5 g, 11.6 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-a3100613125448ef867ddb0910b71a8e
Source dataset
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09045389B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes