Pyridine → 2,2,3,3-Tetrafluoro-3-methoxypropanenitrile

HRID 2198383Notes

Reaction equation

HRID 2198383 reaction equation
[CH3:1][O:2][C:3]([F:11])([F:10])[C:4]([F:9])([F:8])[C:5]([NH2:7])=O.N1C=CC=CC=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O>COCCOCCOC>[CH3:1][O:2][C:3]([F:11])([F:10])[C:4]([F:9])([F:8])[C:5]#[N:7]

Participants

5

Reactant 3

HCID 1049PyridineHCID 9845Trifluoroacetic anhydrideHCID 205200792,2,3,3-Tetrafluoro-3-methoxypropanamide

Product 1

HCID 205200812,2,3,3-Tetrafluoro-3-methoxypropanenitrileYield 77.5%

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Procedure

A solution of 52.5 g (0.30 mol) of the amide from Part A in 200 ml of diglyme was stirred at -10° while 47.5 g (0.60 mol) of pyridine and then 63.0 g (0.30 mol) of trifluoroacetic anhydride were added. The cooling bath was removed, and the mixture was stirred at about 25° for 2 h. Evaporation of volatiles to 40° (4.5 mm) gave 42.7 g of crude product, which was distilled to afford 36.5 g (77%) of 3-methoxytetrafluoropropionitrile, b.p. 53°. IR (neat): 3.36 and 3.48 (sat'd CH), 4.42 (CN), 8-10μ (CF, C--O). NMR: 1H 3.78 ppm (s, OCH3): 19F -93.2 (t, JFF 6.3 Hz, 2F, CH2) and -108.8 ppm (t, JFF 6.3 Hz, 2F, CF2). Elemental analysis was consistent with the formula C4H3F4NO. ##STR54##

Workup

  1. customThe cooling bath was removed
  2. customEvaporation of volatiles to 40° (4.5 mm)
  3. customgave 42.7 g of crude product, which
  4. distillationwas distilled

Sources & evidence

ORD record
ord-22c58637593546acb6a643dbefab100f
Source dataset
uspto-grants-1982_11
Patent number
US04357282

Reaction notes

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