Cesium carbonate → Tert-butyl 2-((5-(4-(trifluoromethoxy)phenyl)benzo[d]isoxazol-3-yl)oxy)acetate

HRID 1482874Notes

Reaction equation

HRID 1482874 reaction equation
[F:1][C:2]([F:21])([F:20])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[CH:12][C:13]3[O:17][N:16]=[C:15]([OH:18])[C:14]=3[CH:19]=2)=[CH:6][CH:5]=1.Br[CH2:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.C(OCC)(=O)C>[F:21][C:2]([F:1])([F:20])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[CH:12][C:13]3[O:17][N:16]=[C:15]([O:18][CH2:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C:14]=3[CH:19]=2)=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 79177tert-Butyl bromoacetateHCID 178518982HCID 178518982, compound

Product 1

HCID 118161964Tert-butyl 2-((5-(4-(trifluoromethoxy)phenyl)benzo[d]isoxazol-3-yl)oxy)acetateYield 41.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

5-(4-(trifluoromethoxy)phenyl)benzo[d]isoxazol-3-ol (500 mg, 1.69 mmol), tert-butyl 2-bromoacetate (500 mg, 2.56 mmol) and cesium carbonate (1.65 g) were combined in 5 mL DMF and stirred at ambient temperature for 1 hour. The reaction mixture was diluted with 80 mL ethyl acetate, washed with water and brine and evaporated under vacuum. Flash chromatographic purification on 12 g silica gel with 0-100% ethyl acetate in hexane gave tert-butyl 2-((5-(4-(trifluoromethoxy)phenyl)benzo[d]isoxazol-3-yl)oxy)acetate (285 mg, 0.70 mmol).

Workup

  1. washwashed with water and brine
  2. customevaporated under vacuum
  3. customFlash chromatographic purification on 12 g silica gel with 0-100% ethyl acetate in hexane

Sources & evidence

ORD record
ord-99e3a1723f314c6698894f1d37894021
Source dataset
uspto-grants-2016_08
Patent number
US09416115B2

Reaction notes

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