Benzyl Bromide → HCID 12710434, compound

HRID 1731407Notes

Reaction equation

HRID 1731407 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:9][C:10]([C:16]([F:19])([F:18])[F:17])([S-:15])[C:11]([F:14])([F:13])[F:12].CN([S+](N(C)C)N(C)C)C>C(#N)C>[F:12][C:11]([F:13])([F:14])[C:10]([S:15][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)([F:9])[C:16]([F:19])([F:18])[F:17]

Participants

4

Reactant 2

HCID 7498Benzyl BromideHCID 20225809HCID 20225809, compound

Product 1

HCID 12710434HCID 12710434, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Benzyl bromide, 16.76 g (0.098 mol), was added dropwise at 25° to a solution of 0.098 mole of tris(dimethylamino)sulfonium 1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethanethiolate (prepared as in Example 12) in 125 mL of acetonitrile. The reaction mixture was stirred for 18 h and then poured into 500 mL of ice-water. The aqueous mixture was extracted with ether, and the ether extracts were washed with water, dried (MgSO4) and distilled to give 21.31 g (75% yield) of benzyl heptafluoroisopropyl sulfide as a pale yellow liquid: bp 70°-71° (10 mm); 1H NMR (CDCl3) δ4.09 ppm (s, 2H) and 7.27 ppm (s, 5H); 19F NMR (CDCl3) δ-75.2 ppm (d, J=11 Hz, 6F) and -162.6 ppm (septet, J=11 Hz, 1F). Anal. Calcd. for C10H7F7S: C, 41.10; H, 2.41; F, 45.51. Found: C, 40.89; H, 2.45; F, 45.27.

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-14df26adef9e424cbb51e177d2f9a809
Source dataset
uspto-grants-1986_11
Patent number
US04621125

Reaction notes

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