Benzene → HCID 14024762, compound

HRID 1660098Notes

Reaction equation

HRID 1660098 reaction equation
F[C:2](F)(F)[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=O.[F:13][C:14](S(O)(=O)=O)([F:16])[F:15].[K+].[Br-].[CH:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>>[C:2]1([C:3]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:14]([F:16])([F:15])[F:13])[CH:7]=[CH:6][CH:5]=[CH:3][CH:2]=1

Participants

5

Reactant 4

HCID 241BenzeneHCID 99052,2,2-TrifluoroacetophenoneHCID 62406Trifluoromethanesulfonic acidHCID 253877Potassium Bromide

Product 1

HCID 14024762HCID 14024762, compound

Procedure

A mixture of 10.0 g (0.057 mol) trifluoroacetophenone, 100 ml of benzene, and 5 ml of trifluoromethyl sulfonic acid was stirred for 48 hours at room temperature. The product was worked up as in Example 6 to give a white crystalline mass. Thin-layer and high-pressure liquid chromatography indicated the product was a complex mixture of many components. The thin-layer chromatogram under ultraviolet light indicated the presence of many intensely white and blue fluorescent components. The product mixture was column-chromatographed on silica gel, the material then eluted with pentane, collected, and twice rechromatographed to give 6.2 g (35%), of the white crystalline triphenyl compound: m.p. 158°-159° C.; IR (KBr) 1600 and 1590 (Ar), 1150 (C-F), 760 and 695 cm-1 (monosubstituted phenyl); NMR δ 7.18 (broad singlet); mass spectrum m/e, 312 (parent ion), 243 (P-69), 165 (P-147), 120 (P-192). Analytical: calculated for C20H15F3 ; C, 76.92; H, 4.81; F, 18.2%. Found: C, 76.77; H, 4.84; F, 17.9%.

Workup

  1. customto give a white crystalline mass
  2. additiona complex mixture of many components
  3. customThe product mixture was column-chromatographed on silica gel
  4. washthe material then eluted with pentane
  5. customcollected
  6. customtwice rechromatographed
  7. customto give 6.2 g (35%)

Sources & evidence

ORD record
ord-41fece7406e245bf84e141f692c3c235
Source dataset
uspto-grants-1981_12
Patent number
US04307024

Reaction notes

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