Formic Acid → 2-Fluoro-5-(trifluoromethyl)benzaldehyde

HRID 2395605Notes

Reaction equation

HRID 2395605 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][C:3]=1[C:4]#N.C(O)=[O:15].O>[Ni].C(Cl)Cl>[F:1][C:2]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][C:3]=1[CH:4]=[O:15]

Participants

6

Reactant 3

HCID 284Formic AcidHCID 962Water2×HCID 5210162-Fluoro-5-(trifluoromethyl)benzonitrile

Product 1

HCID 27349042-Fluoro-5-(trifluoromethyl)benzaldehyde

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 18.7 g (0.0988 mol) of 2-fluoro-5-(trifluoromethyl)benzonitrile (prepared according to G. C. Finger et al., Chem. Comm., 1965, 430), 398 ml of 90% formic acid, 296 ml of water and 17.5 g of Raney nickel is heated for 5 hours at reflux and is then left standing overnight. The mixture is poured into 2.5 liters of water and extraction is carried out with methylene chloride (once 1 l and two times 500 ml). Filtration, washing with water, drying over Na2SO4, filtration and distillation are carried out. Yd.: 10.1 g (53%) B.p.14 =70°-72° C. IR: νc-o =1680 cm-1

Workup

  1. temperatureis heated for 5 hours
  2. temperatureat reflux
  3. waitis then left
  4. filtrationFiltration
  5. washwashing with water
  6. dry with materialdrying over Na2SO4, filtration and distillation
  7. custom10.1 g (53%) B.p.14 =70°-72° C

Sources & evidence

ORD record
ord-9baaf003fbb44c36911903f3e713c946
Source dataset
uspto-grants-1996_02
Patent number
US05489592

Reaction notes

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