Water → HCID 13765567, compound

HRID 1731402Notes

Reaction equation

HRID 1731402 reaction equation
Br[CH:2]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[F:15][C:16]([F:19])([F:18])[O-:17].CN([S+](N(C)C)N(C)C)C.O>C(#N)C>[C:3]1([CH:2]([O:17][C:16]([F:19])([F:18])[F:15])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 962WaterHCID 236603BromodiphenylmethaneHCID 22448444Tris(dimethylamino)sulfanium trifluoromethanolate

Product 1

HCID 13765567HCID 13765567, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Bromodiphenylmethane, 20.7 g (0.084 mol), was added portionwise at 25° to a stirred solution of 0.093 mole of tris(dimethylamino)sulfonium trifluoromethoxide (prepared as in Example 1) in 75 mL of acetonitrile. The reaction mixture was stirred for 18 h and then poured into water. The aqueous mixture was extracted with ether, and the ether extracts were washed with water, dried (MgSO4), and then distilled to give 8.34 g of trifluoromethyl diphenylmethyl ether as a colorless oil: bp 83.3° (0.7 mm); 1H NMR (CDCl3) δ6.17 ppm (s, 1H), 7.27 ppm (m, 10H); 19F NMR (CDCl3) δ-58.4 ppm (s). Anal. Calcd. for C14H11F3O: C, 66.66; H, 4.40; F, 22.60. Found: C, 66.82; H, 4.57; F, 22.39.

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-ad29697e1081459a9c5d10578a020fec
Source dataset
uspto-grants-1986_11
Patent number
US04621125

Reaction notes

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