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

HRID 346970

Reaction equation

HRID 346970 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) 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 CH2Cl2 and CH3OH. The organic layer was dried (MgSO4), filtered off and evaporated till dryness. The residue was taken up in Et2O, 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 CH2Cl2 and CH3OH
  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-d279aa93bcb64ec0a3f9cb083911bb48
Source dataset
uspto-grants-2007_02
Patent number
US07173040B2

Linked notes

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