Potassium Carbonate → HCID 19068185, compound

HRID 1957530Notes

Reaction equation

HRID 1957530 reaction equation
[OH:1][C:2]1[CH:13]=[CH:12][C:5]2[C:6]([C:9](=[O:11])[CH3:10])=[N:7][O:8][C:4]=2[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[CH:23]=1>CC(C)=O>[F:29][C:28]([F:30])([F:31])[C:24]1[CH:23]=[C:22]([CH:27]=[CH:26][CH:25]=1)[CH2:21][O:1][C:2]1[CH:13]=[CH:12][C:5]2[C:6]([C:9](=[O:11])[CH3:10])=[N:7][O:8][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1230611-(Bromomethyl)-3-(trifluoromethyl)benzeneHCID 135848334HCID 135848334, compound

Product 1

HCID 19068185HCID 19068185, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2 g of 1-(6-hydroxy-1,2-benzisoxazol-3-yl)ethanone are dissolved in 20 ml of acetone, 2.1 g of potassium carbonate are added and then 3 g of 1-(bromomethyl)-3-(trifluoromethyl)benzene are added dropwise. The reaction mixture is then refluxed for 1 h. After cooling and filtration and concentrating the filtrate under vacuum, the crude product is taken up in ethyl acetate, the organic phase is washed once with water and once with a saturated solution of sodium chloride, dried over sodium sulfate and concentrated. Recrystallistion from ethyl acetate/hexane gives 1-(6-[3-(trifluoromethyl)benzyloxy]-1,2-benzisoxazol-3-yl)ethanone having a melting point of 130°-132° C.

Workup

  1. temperatureThe reaction mixture is then refluxed for 1 h
  2. temperatureAfter cooling
  3. filtrationfiltration
  4. concentrationconcentrating the filtrate under vacuum
  5. washthe organic phase is washed once with water and once with a saturated solution of sodium chloride
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-9529b2d538104a46b9cc8bd8d6cf6b1c
Source dataset
uspto-grants-1998_07
Patent number
US05786374

Reaction notes

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