Methanol → 5-Bromo-3-(3-chlorophenyl)-2,1-benzisoxazole

HRID 1830795Notes

Reaction equation

HRID 1830795 reaction equation
[OH-].[Na+].CO.[Br:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=O)=[CH:8][CH:7]=1.[Cl:15][C:16]1[CH:17]=[C:18]([CH2:22]C#N)[CH:19]=[CH:20][CH:21]=1>O>[Br:5][C:6]1[CH:7]=[CH:8][C:9]2[C:10]([CH:11]=1)=[C:22]([C:18]1[CH:19]=[CH:20][CH:21]=[C:16]([Cl:15])[CH:17]=1)[O:14][N:12]=2

Participants

6

Reactant 4

HCID 887MethanolHCID 114661-Bromo-4-nitrobenzeneHCID 14798Sodium HydroxideHCID 73722m-Chlorophenylacetonitrile

Product 1

HCID 120166705-Bromo-3-(3-chlorophenyl)-2,1-benzisoxazoleYield 34.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium hydroxide (0.62 mol) was dissolved in methanol (100 mol) and the mixture was cooled till room temperature. 1-bromo-4-nitro-benzene (0.124 mol), followed by 3-chloro-benzeneacetonitrile (0.223 mol) were added dropwise, the temperature raised till 50° C. and the mixture was stirred at room temperature for one night. The mixture was poured into water and ice, the precipitate was filtered off, washed with water and extracted with DME and methanol. The organic layer was dried (MgSO4), filtered off and evaporated till dryness. The residue was taken up in diethylether, filtered off and dried, yielding 13.2 g (34.8%) of 5-bromo-3-(3-chlorophenyl)-2,1-benzisoxazole, mp. 163° C. (intermediate 1).

Workup

  1. additionwere added dropwise
  2. temperaturethe temperature raised till 50° C.
  3. filtrationthe precipitate was filtered off
  4. washwashed with water
  5. extractionextracted with DME and methanol
  6. dry with materialThe organic layer was dried (MgSO4)
  7. filtrationfiltered off
  8. customevaporated till dryness
  9. filtrationfiltered off
  10. customdried

Sources & evidence

ORD record
ord-d43f8168d14e4e5a9ea48f992ca7aae4
Source dataset
uspto-grants-2006_06
Patent number
US07067531B2

Reaction notes

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