Dimethyl Sulfate → Methyl 3-cyano-2,2,3,3-tetrafluoropropionate

HRID 231999Notes

Reaction equation

HRID 231999 reaction equation
[C:1]([C:3]([F:11])([F:10])[C:4]([F:9])([F:8])[C:5]([O-:7])=[O:6])#[N:2].[Na+].S(OC)(O[CH3:17])(=O)=O>>[C:1]([C:3]([F:10])([F:11])[C:4]([F:8])([F:9])[C:5]([O:7][CH3:17])=[O:6])#[N:2]

Participants

3

Reactant 2

HCID 6497Dimethyl SulfateHCID 23683599Sodium 3-cyanotetrafluoropropionate

Product 1

HCID 13328902Methyl 3-cyano-2,2,3,3-tetrafluoropropionateYield 58%

Procedure

After being maintained at about 25° for 2 more days, the reaction mixture, which contained sodium 3-cyanotetrafluoropropionate, was treated with 69.3 g (0.55 mole) of dimethyl sulfate, stirred, and allowed to stand overnight. Fractionation of the volatile products gave 53.3 g (58%) of methyl 3-cyanotetrafluoropropionate, bp 90°-97°.

Workup

  1. temperatureAfter being maintained at about 25° for 2 more days

Sources & evidence

ORD record
ord-7277011a39714591b1a5a78b80d3d4a3
Source dataset
uspto-grants-1989_07
Patent number
US04851161

Reaction notes

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