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

HRID 510586Notes

Reaction equation

HRID 510586 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-6e93e24f57ed4f2eaee1874c26441e06
Source dataset
uspto-grants-2015_08
Patent number
US09096567B2

Reaction notes

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