Benzyl Bromide → HCID 13765565, compound

HRID 1731400Notes

Reaction equation

HRID 1731400 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:9][C:10]([F:13])([F:12])[O-:11].CN([S+](N(C)C)N(C)C)C>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:13])[F:12]

Participants

4

Reactant 2

HCID 7498Benzyl BromideHCID 22448444Tris(dimethylamino)sulfanium trifluoromethanolate

Product 1

HCID 13765565HCID 13765565, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Benzyl bromide, 12.47 g (0.073 mol), was added dropwise at 25° to a solution of 0.081 mol of tris(dimethylamino)sulfonium trifluoromethoxide (prepared as in Example 1) in 75 mL of acetonitrile. The reaction mixture was stirred at 25° for 18 h and then poured into ice-water. The aqueous mixture was extracted with ether, and the ether extracts were washed with water, dried (MgSO4), and distilled to give 10.55 g (85%) of benzyl trifluoromethyl ether as a colorless oil: bp 45°-46° (18 mm); 1H NMR (CDCl3) δ4.93 ppm (s, 2H), 7.33 ppm (s, 5H); 19F NMR (CDCl3) δ-60.6 ppm (s). Anal. Calcd. for C8H7F3O: C, 54.55; H, 4.01; F, 32.36. Found: C, 54.76; H, 4.04; F, 32.51.

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-8c4670b412124403aac1e3ab6549d9fc
Source dataset
uspto-grants-1986_11
Patent number
US04621125

Reaction notes

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