Dimethyl Sulfoxide → 4-(Benzoxazol-2-yl)-2-fluorophenylacetonitrile

HRID 2071474Notes

Reaction equation

HRID 2071474 reaction equation
[C-:1]#[N:2].[Na+].CS(C)=O.Br[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[O:17][C:18]3[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=3[N:20]=2)=[CH:12][C:11]=1[F:25]>O>[O:17]1[C:18]2[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=2[N:20]=[C:16]1[C:13]1[CH:14]=[CH:15][C:10]([CH2:9][C:1]#[N:2])=[C:11]([F:25])[CH:12]=1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 8929Sodium CyanideHCID 21413805HCID 21413805, compound

Product 1

HCID 102146254-(Benzoxazol-2-yl)-2-fluorophenylacetonitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 0.6 gm. of sodium cyanide in 25 ml. of dimethyl sulfoxide preheated to 65°-70° C. is slowly added 2.5 gm. of 2-(4-bromomethyl-3-fluorophenyl)benzoxazole. The reaction mixture is heated at 60°-70° C. for 1 hour, then cooled and poured into water. The resulting precipitate is filtered off and chromatographed on 300 gm. of silica gel. Elution with methylene chloride gives 4-(benzoxazol-2-yl)-2-fluorophenylacetonitrile.

Workup

  1. custompreheated to 65°-70° C.
  2. temperatureThe reaction mixture is heated at 60°-70° C. for 1 hour
  3. temperaturecooled
  4. filtrationThe resulting precipitate is filtered off
  5. customchromatographed on 300 gm
  6. washElution with methylene chloride

Sources & evidence

ORD record
ord-65bfa1254b3d4857a953360b75123b71
Source dataset
uspto-grants-1977_09
Patent number
US04046905

Reaction notes

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