Acetic Acid → 2-Amino-5-bromobenzophenone

HRID 463490Notes

Reaction equation

HRID 463490 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]([CH:16]=1)=[C:7]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[O:8][N:9]=2.C(O)(=O)C>[Zn].O>[NH2:9][C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:16][C:6]=1[C:7]([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)=[O:8]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 3472905-Bromo-3-phenyl-2,1-benzisoxazole

Product 1

HCID 996772-Amino-5-bromobenzophenoneYield 94%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

5-Bromo-3-phenyl-2,1-benzisoxazole (7.5 g, 28.6 mmol), water (14.6 ml), and zinc dust (9.3 g, 143 mmol) were combined. Acetic acid (8.6 ml, 143 mmol) was added and the mixture was stirred and heated at 80° C. for 90 minutes. After cooling to room temperature, both the liquid and solid portion of the reaction were extracted with methylene chloride. The combined methylene chloride solutions was washed once with sodium hydroxide solution (10%) and several times with water. Drying (sodium sulfate) and evaporation yielded the desired product (7.42 g) of mp. 92°-102° C.

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionthe liquid and solid portion of the reaction were extracted with methylene chloride
  3. washThe combined methylene chloride solutions was washed once with sodium hydroxide solution (10%) and several times with water
  4. customDrying
  5. custom(sodium sulfate) and evaporation

Sources & evidence

ORD record
ord-b7e3e13aa1b94319bbd3a75180d2377c
Source dataset
uspto-grants-1985_05
Patent number
US04519937

Reaction notes

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