Phenacyl bromide → 104159-53-7

HRID 1731401Notes

Reaction equation

HRID 1731401 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].[F:11][C:12]([F:15])([F:14])[O-:13].CN([S+](N(C)C)N(C)C)C>C(#N)C>[F:11][C:12]([F:15])([F:14])[O:13][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4]

Participants

4

Reactant 2

HCID 6259Phenacyl bromideHCID 22448444Tris(dimethylamino)sulfanium trifluoromethanolate

Product 1

HCID 13765566104159-53-7

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

α-Bromoacetophenone, 13.61 g (0.068 mol), was added dropwise at 25° to a solution of 0.076 mol of tris(dimethylamino)sulfonium trifluoromethoxide (prepared as in Example 1) in 75 mL of acetonitrile. The reaction mixture was stirred for 3 days 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 α-trifluoromethoxyacetophenone as a colorless liquid: bp 64°-65° (0.8 mm); 1H NMR (CDCl3) δ5.15 ppm (s, 2H), 7.50 ppm (m, 3H), 7.85 ppm (m, 2H); 19F NMR (CDCl3) δ-61.5 ppm(s).

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-a4ae467a9f2d4300a4fc5019deceb7a2
Source dataset
uspto-grants-1986_11
Patent number
US04621125

Reaction notes

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