Water → 3-(4-Chlorophenyl)-2,1-benzisoxazole-7-acetonitrile

HRID 1198997Notes

Reaction equation

HRID 1198997 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][N:10]=[C:11]3[C:16]([CH2:17]Br)=[CH:15][CH:14]=[CH:13][C:12]=23)=[CH:4][CH:3]=1.[C-:19]#[N:20].[K+].O1CCOCC1.O>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][N:10]=[C:11]3[C:16]([CH2:17][C:19]#[N:20])=[CH:15][CH:14]=[CH:13][C:12]=23)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 9032Potassium CyanideHCID 312751,4-DioxaneHCID 156347563-(4-Chlorophenyl)-7-(bromomethyl)-2,1-benzisoxazole

Product 1

HCID 156347583-(4-Chlorophenyl)-2,1-benzisoxazole-7-acetonitrileYield 61%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 11.5 g (0.036 mole) of crude 3-(4-chlorophenyl)-7-(bromomethyl)-2,1-benzisoxazole, 9.8 g (0.15 mole) of potassium cyanide, 150 ml of dioxane and 75 ml of water was heated at reflux under a nitrogen atmosphere for 2.5 hr. The solution was cooled and poured into 400 ml of methylene chloride. The layers were separated and the organic layer was washed with four 200 ml portions of water, dried over sodium sulfate, and concentrated to give a solid as residue. The solid was recrystallized (charcoal) twice from ethyl acetate to yield 5.8 g (61%) of crystals, m.p. 165°-169° C.

Workup

  1. temperatureat reflux under a nitrogen atmosphere for 2.5 hr
  2. temperatureThe solution was cooled
  3. customThe layers were separated
  4. washthe organic layer was washed with four 200 ml portions of water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customto give a solid as residue
  8. customThe solid was recrystallized (charcoal) twice from ethyl acetate

Sources & evidence

ORD record
ord-aaa339ad2e124f8c975149d421083d32
Source dataset
uspto-grants-1990_02
Patent number
US04898874

Reaction notes

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