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

HRID 1294636Notes

Reaction equation

HRID 1294636 reaction equation
[OH-].[Na+].[Br:3][C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=O)=[CH:6][CH:5]=1.[Cl:13][C:14]1[CH:15]=[C:16]([CH2:20]C#N)[CH:17]=[CH:18][CH:19]=1.O>CO>[Br:3][C:4]1[CH:5]=[CH:6][C:7]2[C:8]([CH:9]=1)=[C:20]([C:16]1[CH:17]=[CH:18][CH:19]=[C:14]([Cl:13])[CH:15]=1)[O:12][N:10]=2

Participants

6

Reactant 4

HCID 962WaterHCID 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 887MethanolSolvent

Procedure

Sodium hydroxide (0.62 mol) was dissolved in methanol (100 ml) and the mixture was cooled till room temperature. 1-Bromo-4-nitro-benzene (0.124 mol), followed by 3-chloro-benzeneacetonitrile (0.223 mol) was added dropwise, the temperature rose 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 DCM 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. additionwas added dropwise
  2. customrose till 50° C.
  3. filtrationthe precipitate was filtered off
  4. washwashed with water
  5. extractionextracted with DCM 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-2430ade0e4d940e6932460435200fc95
Source dataset
uspto-grants-2007_07
Patent number
US07241777B2

Reaction notes

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