Hypofluorous acid, trifluoromethyl ester → HCID 11107832, compound

HRID 2058289Notes

Reaction equation

HRID 2058289 reaction equation
[CH2:1]([O:3][C:4]([O:17][Si](C)(C)C)=[C:5]([CH3:16])[C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH:13]([CH3:15])[CH3:14])=[CH:8][CH:7]=1)[CH3:2].[F:22]OC(F)(F)F>C(Cl)(Cl)(Cl)F>[F:22][C:5]([C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH:13]([CH3:15])[CH3:14])=[CH:8][CH:7]=1)([CH3:16])[C:4]([O:3][CH2:1][CH3:2])=[O:17]

Participants

4

Reactant 2

HCID 78989Hypofluorous acid, trifluoromethyl esterHCID 54497858HCID 54497858, compound

Product 1

HCID 11107832HCID 11107832, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6389TrichlorofluoromethaneSolvent

Procedure

A solution of 27.59 g (0.09 mol) of β-ethoxy-4-isobutyl-α-methyl-β-(trimethylsiloxy)styrene in 250 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 4 hours. The reaction mixture then was warmed to room temperature and distilled to give 19.3 g (85% yield) of ethyl α-fluoro-4-isobutyl-α-methylphenylacetate as a colorless liquid; bp 88°-89° C. (0.4 mm); 19F NMR (CDCl3) δ 150.9 ppm (q, J=22.5 Hz); 1H NMR (CDCl3) α 0.91 ppm (d, J=6 Hz, 6H), 1.22 ppm (t, J=7 Hz, 3H), 1.88 ppm (m, 1H), 1.91 ppm (d, J=22.5 Hz, 3H), 2.48 ppm (d, J=6 Hz, 2H), 4.21 ppm (q, J= 7 Hz, 2H) and 7.0-7.6 ppm (m, 4H). Anal. Calcd. for C15H21FO2 : C, 71.40; H, 8.39; F, 7.53; Found: C, 71.63; H, 8.35; F, 7.43.

Workup

  1. distillationdistilled

Sources & evidence

ORD record
ord-995e2c93f5994331985d8cc8e84fce0e
Source dataset
uspto-grants-1980_07
Patent number
US04215044

Reaction notes

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