Hypofluorous acid, trifluoromethyl ester → HCID 10866965, compound

HRID 2058281Notes

Reaction equation

HRID 2058281 reaction equation
[CH2:1]([O:3][C:4]([O:12][Si](C)(C)C)=[CH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH3:2].[F:17]OC(F)(F)F>C(Cl)(Cl)(Cl)F>[F:17][CH:5]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:4]([O:3][CH2:1][CH3:2])=[O:12]

Participants

4

Reactant 2

HCID 78989Hypofluorous acid, trifluoromethyl esterHCID 54532677HCID 54532677, compound

Product 1

HCID 10866965HCID 10866965, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6389TrichlorofluoromethaneSolvent

Procedure

A solution of 21.28 g (0.09 mol) of β-ethoxy-β-trimethylsiloxystyrene (from above) in 200 ml of CFCl3 was cooled to -70° C. and 9.4 g (0.09 mol) of trifluoromethyl hypofluorite were passed into the solution over a period of 3 hours. The reaction mixture was warmed to room temperature and then distilled to give 12.52 g (77% yield) of ethyl α-fluorobenzeneacetate as a colorless liquid: bp 96°-98° C. (4.8 mm); 19F NMR (CFCl3) δ-180.1 ppm (d,J=48 Hz); 1H NMR (CFCl3) δ 1.10 ppm (t,J=7 Hz, 2H), 4.10 ppm (q,J=7 Hz, 2H), 5.66 ppm (d,J=48 Hz, 1H) and 7.1-7.6 ppm (m, 5H). Anal. Calcd. for C10H11FO2 : C, 65.92; H, 6.07; F, 10.43; Found: C, 66.09; H, 6.13; F, 10.33.

Workup

  1. distillationdistilled

Sources & evidence

ORD record
ord-1eb0259f93ae47f2a26e3ab63c843aaa
Source dataset
uspto-grants-1980_07
Patent number
US04215044

Reaction notes

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