Water → 2-Amino-5-bromobenzophenone

HRID 1380011Notes

Reaction equation

HRID 1380011 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.O>[Zn].C(O)(=O)C>[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 962WaterHCID 3472905-Bromo-3-phenyl-2,1-benzisoxazole

Product 1

HCID 996772-Amino-5-bromobenzophenoneYield 98.2%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

5-Bromo-3-phenyl-2,1-benzisoxazole (7.5 g, 28.6 m mol), water (14.6 ml), and zinc dust (9.3 g, 143 m mol) were combined. Acetic acid (8.6 ml, 143 m mol) 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-6fd43e89e2a34b53ab541e0d05e92354
Source dataset
uspto-grants-1986_04
Patent number
US04579679

Reaction notes

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