Dimethylformamide → 2-Ethoxy-6-fluorobenzaldehyde

HRID 2257803Notes

Reaction equation

HRID 2257803 reaction equation
C([Li])CCC.CCCCCC.[CH2:12]([O:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[CH:16]=1)[CH3:13].CN([CH:25]=[O:26])C>C1COCC1>[CH2:12]([O:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[C:16]=1[CH:25]=[O:26])[CH3:13]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8058HexaneHCID 1363011-Ethoxy-3-fluorobenzeneHCID 178418339Butyllithium

Product 1

HCID 38158942-Ethoxy-6-fluorobenzaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-65 °C

Procedure

1.6M Butyl lithium in hexane (24 ml, 38.4 mmol) was added slowly (0.5 h) to a solution of 1-ethoxy-3-fluorobenzene (5.0 g, 35.7 mmol) in 100 ml of dry THF at -65° C. under nitrogen. The solution was stirred at -65° C. for 25 min. DMF (5.22 g, 71.4 mmol) was added dropwise to the solution. The mixture was allowed to warm to room temperature. 300 ml of ice was poured to this mixture and it was extracted with diethyl ether. Diethyl ether was washed with brine, dried over Na2SO4 and evaporated. The product was purified by silica gel column chromatography (EtOAc/petroleum ether 10:100) to give 2-ethoxy-6-fluorobenzaldehyde.

Workup

  1. temperatureto warm to room temperature
  2. extractionwas extracted with diethyl ether
  3. washDiethyl ether was washed with brine
  4. dry with materialdried over Na2SO4
  5. customevaporated
  6. customThe product was purified by silica gel column chromatography (EtOAc/petroleum ether 10:100)

Sources & evidence

ORD record
ord-ceb6730929f14f10a4d67544dc50bcca
Source dataset
uspto-grants-1997_08
Patent number
US05658907

Reaction notes

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