Trichlorofluoromethane → Trifluoromethylsilyl alpha-fluoro-4-(2-methylpropyl)benzeneacetate

HRID 2058294Notes

Reaction equation

[CH3:1][CH:2]([CH3:22])[CH2:3][C:4]1[CH:21]=[CH:20][C:7]([CH:8]=[C:9]([O:15][Si:16](C)(C)C)[O:10][Si](C)(C)C)=[CH:6][CH:5]=1.FO[C:25]([F:28])([F:27])[F:26].C(Cl)(Cl)(Cl)[F:30]>>[F:30][CH:8]([C:7]1[CH:20]=[CH:21][C:4]([CH2:3][CH:2]([CH3:22])[CH3:1])=[CH:5][CH:6]=1)[C:9]([O:15][SiH2:16][C:25]([F:28])([F:27])[F:26])=[O:10]

Participants

Reactant 3

HCID 6389Trichlorofluoromethane

HCID 78989Hypofluorous acid, trifluoromethyl ester

HCID 126020994-(2-Methylpropyl)-beta,beta-bis(trimethylsiloxy)styrene

Product 1

HCID 124016670Trifluoromethylsilyl alpha-fluoro-4-(2-methylpropyl)benzeneacetateYield 100%

Conditions

Temperature: 25 °C

Procedure

A solution of 16.8 g (0.05 mol) of the aforesaid 4-(2-methylpropyl)-β,β-bis(trimethylsiloxy)-styrene in 250 ml of CFCl3 was cooled to -70° C. and 5.2 g (0.05 mol) of trifluoromethyl hypofluorite were passed into the solution over a period of 1 hour. The reaction mixture was warmed to room temperature (25° C.) and then evaporated under reduced pressure to give 14.1 g (100% yield) of crude trifluoromethylsilyl α-fluoro-4-(2-methylpropyl)benzeneacetate as a colorless oil: 19F NMR (CFCl3) δ-176.8 ppm (d, J=49 Hz); 1H NMR (CFCl3, ext. TMS) δ 0.01 ppm (s, 9H), 0.66 ppm (d, J=6 Hz, 6H), 1.55 ppm (m, 1H), 2.22 ppm (d, J=6 Hz, 2H), 5.30 ppm (d, J=49 Hz, 1H) and 6.7-7.2 ppm (A 2 B2).

Workup

customevaporated under reduced pressure

Sources & evidence

ORD record: ord-96e182ada12c4853ada231f9366a35f6
Source dataset: uspto-grants-1980_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04215044

Reaction notes

Loading…