Water → HCID 13765570, compound

HRID 1731405Notes

Reaction equation

HRID 1731405 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:9][C:10]([F:22])([C:12]([F:21])([C:17]([F:20])([F:19])[F:18])[C:13]([F:16])([F:15])[F:14])[O-:11].CN([S+](N(C)C)N(C)C)C.O>C(#N)C>[F:9][C:10]([O:11][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)([F:22])[C:12]([F:21])([C:13]([F:15])([F:14])[F:16])[C:17]([F:20])([F:19])[F:18]

Participants

5

Reactant 3

HCID 962WaterHCID 7498Benzyl BromideHCID 20225799HCID 20225799, compound

Product 1

HCID 13765570HCID 13765570, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Benzyl bromide, 10.62 g (0.0621 mol), was added dropwise to a solution of 27.5 g (0.069 mol) of tris(dimethylamino)sulfonium 1,1,2,3,3,3-hexafluoro-2-(trifluoromethyl)propoxide (prepared as in Example 7) in 50 mL of acetonitrile at 25°. The reaction mixture was stirred for 2 h and then poured into water. The aqueous mixture was extracted with ether, and the ether extracts were washed with water, dried (MgSO4), and distilled to give benzyl 1,1,2,3,3,3-hexafluoro-2-(trifluoromethyl)propyl ether as a colorless liquid: bp 86°-87° (36 mm); 19F NMR (CDCl3) δ-73.9 ppm (t, d, J=9, 6 Hz, 6F), -79.2 ppm (d, septet, J=9, 9 Hz, 2F), and -187.7 ppm (t, septet, J=9, 6 Hz, 1F). Anal. Calcd. for C11H7F9O: C, 40.50; H, 2.16. Found: C, 40.69; H, 2.29.

Workup

  1. extractionThe aqueous mixture was extracted with ether
  2. washthe ether extracts were washed with water
  3. dry with materialdried (MgSO4)
  4. distillationdistilled

Sources & evidence

ORD record
ord-b6f6edc5d1214ed68d7e660cf45de420
Source dataset
uspto-grants-1986_11
Patent number
US04621125

Reaction notes

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