Cesium fluoride → 3-(4-Bromophenyl)isoxazole

HRID 736395Notes

Reaction equation

HRID 736395 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[C:11]([Si](C)(C)C)[O:10][N:9]=2)=[CH:4][CH:3]=1.[F-].[Cs+]>CCO.CC#N.[NH4+].[Cl-]>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:12]=[CH:11][O:10][N:9]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 2

HCID 25953Cesium fluorideHCID 221704493-(4-Bromophenyl)-5-(trimethylsilyl)isoxazole

Product 1

HCID 126477523-(4-Bromophenyl)isoxazole

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 6342AcetonitrileSolventHCID 25517Ammonium ChlorideSolvent

Procedure

The product from Example 42B (0.103 g) in EtOH (0.7 mL) and MeCN (2.1 mL) was treated with CsF (72 mg, 0.47 mmol), stirred for 5 minutes, diluted with saturated NH4Cl (7 mL), and extracted with CH2Cl2 (2×7 mL). The organic extract was dried (Na2SO4), filtered, and the filtrate concentrated under reduced pressure. The residue was purified by flash chromatography (7% ethyl acetate in hexanes) to provide the title compound.

Workup

  1. extractionextracted with CH2Cl2 (2×7 mL)
  2. extractionThe organic extract
  3. dry with materialwas dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated under reduced pressure
  6. customThe residue was purified by flash chromatography (7% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-1ae4e0a1849e45e98ce4bedb40516b44
Source dataset
uspto-grants-2009_09
Patent number
US07595332B2

Reaction notes

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