2-Fluoro-4-(trifluoromethyl)benzaldehyde → 2-Methoxy-4-(trifluoromethyl)benzaldehyde

HRID 1047980Notes

Reaction equation

HRID 1047980 reaction equation
F[C:2]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[CH3:14][O-:15].[Na+]>>[CH3:14][O:15][C:2]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5]

Participants

3

Reactant 2

HCID 5229292-Fluoro-4-(trifluoromethyl)benzaldehydeHCID 10942334Sodium Methoxide

Product 1

HCID 49847042-Methoxy-4-(trifluoromethyl)benzaldehydeYield 85%

Conditions

Temperature
50 °C

Procedure

2-Fluoro-4-(trifluoromethyl)benzaldehyde (5.0 g, 26 mmol) was diluted with sodium methoxide (57 ml of 0.5 M in methanol; 29 mmol), heated to 50° C. and stirred for 6 hours. The reaction was then partially concentrated, diluted with ethyl acetate and water. The layers were separated and the organic layer was dried over MgSO4, filtered and concentrated to yield 2-methoxy-4-(trifluoromethyl)benzaldehyde (4.5 g, 22 mmol, 85% yield).

Workup

  1. concentrationThe reaction was then partially concentrated
  2. additiondiluted with ethyl acetate and water
  3. customThe layers were separated
  4. dry with materialthe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-0adb9044bfc44a37ac99171997c235d7
Source dataset
uspto-grants-2013_10
Patent number
US08569522B2

Reaction notes

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