Dimethylformamide → 2-Ethoxy-6-fluorobenzaldehyde

HRID 233724Notes

Reaction equation

HRID 233724 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-e7f27b62e72e4787a3bfa34734ef6781
Source dataset
uspto-grants-1997_01
Patent number
US05593993

Reaction notes

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