Water → Benzene, [3,3,4,4,5,5,5-heptafluoro-2,2-bis(trifluoromethyl)pentyl]-

HRID 485149Notes

Reaction equation

HRID 485149 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:9][C:10]([F:27])([F:26])[C-:11]([C:22]([F:25])([F:24])[F:23])[C:12]([F:21])([F:20])[C:13]([F:19])([F:18])[C:14]([F:17])([F:16])[F:15].CN([S+](N(C)C)N(C)C)C.O>C(#N)C>[F:20][C:12]([F:21])([C:13]([F:18])([F:19])[C:14]([F:15])([F:16])[F:17])[C:11]([C:22]([F:25])([F:24])[F:23])([C:10]([F:27])([F:26])[F:9])[CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 7498Benzyl BromideHCID 20228874Tris(dimethylamino)sulfonium 1,1,1,3,3,4,4,5,5,5-decafluoro-2-(trifluoromethyl)-2-pentanide

Product 1

HCID 11212014Benzene, [3,3,4,4,5,5,5-heptafluoro-2,2-bis(trifluoromethyl)pentyl]-Yield 66%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Benzyl bromide, 4.77 g (0.028 mol), was added dropwise to a solution of 15.0 g (0.031 mol) of tris(dimethylamino)sulfonium 1,1,1,3,3,4,4,5,5,5-decafluoro-2-(trifluoromethyl)-2-pentanide in 50 mL of acetonitrile at 25° C. and the reaction mixture was stirred overnight and then poured into water. The aqueous mixture was extracted with ether, and the ether extracts were dried (MgSO4) and then distilled to give 7.5 g (66%) of 3,3,4,4,5,5,5-heptafluoro-2,2-bis(trifluoromethyl)pentylbenzene as a colorless liquid: b.p. 62°-63° (5 mm); 19F NMR (CDCl3) δ -62.7 ppm (t,t, 6F), -80.7 ppm (t, 3F), -106.3 ppm (m, 2F) and -123.3 ppm (2F); 1H NMR (CDCl3) δ 3.52 ppm (s, 2H) and 7.27 ppm (s, 5H). Anal. Calcd. for C13H7F13 : C, 38.07; H, 1.72; F, 60.21. Found: C, 37.82; H, 1.73; F, 60.42.

Workup

  1. extractionThe aqueous mixture was extracted with ether
  2. dry with materialthe ether extracts were dried (MgSO4)
  3. distillationdistilled

Sources & evidence

ORD record
ord-e5edefd9215c409fb12591ec74066475
Source dataset
uspto-grants-1985_08
Patent number
US04535184

Reaction notes

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