Hypofluorous acid, trifluoromethyl ester → 2-Fluoro-1,2-diphenylethan-1-one

HRID 2058287Notes

Reaction equation

HRID 2058287 reaction equation
C[Si](C)(C)[O:3][C:4](=[CH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[F:20]OC(F)(F)F>ClC(F)(F)F>[F:20][CH:11]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:4]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:3]

Participants

4

Reactant 2

HCID 78989Hypofluorous acid, trifluoromethyl esterHCID 54215140HCID 54215140, compound

Product 1

HCID 125706862-Fluoro-1,2-diphenylethan-1-oneYield 72.1%

Reagents, catalysts & solvents 1

HCID 6392ChlorotrifluoromethaneSolvent

Procedure

A solution of 18.8 g (0.07 mol) of the aforesaid α-trimethylsiloxystilbene in 200 ml of chlorotrifluoromethane was cooled to -70° C. and 7.3 g (0.07 mol) of trifluoromethyl hypofluorite were passed into the solution over a 3 hour period. The reaction mixture then was warmed to room temperature and evaporated to dryness under reduced pressure to give a white solid. Recrystallization from heptane gave 10.81 g (72% yield) of α-fluoro-α-phenylacetophenone as colorless crystals: mp 50°-51° C.; 19F NMR (CDCl3) δ-176.5 ppm (d, J=49 Hz); 1H NMR (CDCl3) δ 6.52 ppm (d, J=49 Hz, 1H), 7.2-8.2 ppm (m, 10H). Anal. Calcd. for C14H11FO: C, 78.49; H, 5.18; F, 8.87; Found: C, 78.52; H, 5.13; F, 8.65.

Workup

  1. customevaporated to dryness under reduced pressure
  2. customto give a white solid
  3. customRecrystallization from heptane

Sources & evidence

ORD record
ord-cd90807220b14b498a67bb04771a7145
Source dataset
uspto-grants-1980_07
Patent number
US04215044

Reaction notes

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