Nitrobenzene → 3-(4-Fluorophenyl)-2,1-benzisoxazole

HRID 1147

Reaction equation

HRID 1147 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]#N)=[CH:4][CH:3]=1.[OH-].[Na+].[N+:13]([C:16]1C=[CH:20][CH:19]=[CH:18][CH:17]=1)([O-])=[O:14]>CO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:14][N:13]=[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:9]=23)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 7416NitrobenzeneHCID 14798Sodium HydroxideHCID 68016Benzeneacetonitrile, 4-fluoro-

Product 1

HCID 196948213-(4-Fluorophenyl)-2,1-benzisoxazole

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A total of 50.7 g (0.375 mol) of 4-fluorophenyl-acetonitrile is slowly added to a vigorously stirred, room-temperature solution of 150 g (3.75 mol) of sodium hydroxide in 750 ml of absolute methanol. After solution is complete, 46 g (0.374 mol) of nitrobenzene is slowly added. The resulting solution is warmed to 65°-70° C. and held at this temperature for 9 hours. The dark slurry is cooled to room temperature, diluted with 250 ml of 50% methanol, and cooled in an ice bath. The resulting dark precipitate is filtered and washed with cold methanol until the methanol washings were clear. The product (16) is recrystallized from toluene.

Workup

  1. temperatureThe resulting solution is warmed to 65°-70° C.
  2. temperaturecooled in an ice bath
  3. filtrationThe resulting dark precipitate is filtered
  4. washwashed with cold methanol until the methanol washings
  5. customThe product (16) is recrystallized from toluene

Sources & evidence

ORD record
ord-d0e79d3004cd4cb5a98d3c999a726a05
Source dataset
uspto-grants-1998_03
Patent number
US05723573

Linked notes

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