Bromine → 2-Bromo-1,1,1,3,3,4,4,5,5,5-decafluoro-2-(trifluoromethyl)pentane

HRID 485147Notes

Reaction equation

HRID 485147 reaction equation
[Br:1]Br.[F:3][C:4]([F:21])([F:20])[C-:5]([C:16]([F:19])([F:18])[F:17])[C:6]([F:15])([F:14])[C:7]([F:13])([F:12])[C:8]([F:11])([F:10])[F:9].CN([S+](N(C)C)N(C)C)C>C(#N)C1C=CC=CC=1>[Br:1][C:5]([C:16]([F:17])([F:18])[F:19])([C:6]([F:15])([F:14])[C:7]([F:13])([F:12])[C:8]([F:11])([F:10])[F:9])[C:4]([F:20])([F:21])[F:3]

Participants

4

Reactant 2

HCID 24408BromineHCID 20228874Tris(dimethylamino)sulfonium 1,1,1,3,3,4,4,5,5,5-decafluoro-2-(trifluoromethyl)-2-pentanide

Product 1

HCID 27362472-Bromo-1,1,1,3,3,4,4,5,5,5-decafluoro-2-(trifluoromethyl)pentaneYield 75%

Reagents, catalysts & solvents 1

HCID 7505BenzonitrileSolvent

Procedure

Bromine, 7.99 g (0.5 mol), was added dropwise at 0° to a solution of 0.05 mol of tris(dimethylamino)sulfonium 1,1,1,3,3,4,4,5,5,5-decafluoro-2-(trifluoromethyl)-2-pentanide, prepared as in Example D (except for the amounts), in 40 mL of benzonitrile. The reaction mixture was warmed to 25°, and the volatile portion was distilled out under reduced pressure, and then redistilled at atmospheric pressure to give 12.8 g (75%) of 2-bromo-1,1,1,3,3,4,4,5,5,5-decafluoro-2-(trifluoromethy)pentane as a colorless liquid: b.p. 96.5°-97.2°; 19F NMR (CDCl3) δ -65.2 ppm (m, 6F), -81.1 ppm (t, 3F), -105.9 ppm (2F) and -122.6 ppm (2F). Anal. Calcd. for C6BrF13 : C, 18.06; F, 61.91. Found: C, 17.90; F, 61.55.

Workup

  1. temperatureThe reaction mixture was warmed to 25°
  2. distillationthe volatile portion was distilled out under reduced pressure
  3. distillationredistilled at atmospheric pressure

Sources & evidence

ORD record
ord-d6a4ebfeace2442ca4701175088dd609
Source dataset
uspto-grants-1985_08
Patent number
US04535184

Reaction notes

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