Phenacyl bromide → HCID 90203755, compound

HRID 927053Notes

Reaction equation

HRID 927053 reaction equation
[C:1]([O:5][C:6](=[O:20])[NH:7][C:8]1[C:9]([C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=2)=[N:10][O:11][CH:12]=1)([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[K+].[K+].Br[CH2:28][C:29]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:30].O.C(OCC)(=O)C>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C=O)C>[C:1]([O:5][C:6](=[O:20])[NH:7][C:8]1[C:9]([C:13]2[CH:14]=[CH:15][C:16]([O:19][CH2:28][C:29](=[O:30])[C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)=[CH:17][CH:18]=2)=[N:10][O:11][CH:12]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 6259Phenacyl bromideHCID 11430Potassium CarbonateHCID 22728543Water ethylacetateHCID 136491270HCID 136491270, compound

Product 1

HCID 90203755HCID 90203755, compoundYield 98.6%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of [3-(4-hydroxy-phenyl)-isoxazol-4-yl]-carbamic acid tert-butyl ester (50 mg, 0.18 mmol), K2CO3 (33 mg, 0.24 mmol) and tetrabutylammonium iodide (6.7 mg, 0.018 mmol) in DMF (2 mL) was added 2-bromoacetophenone (39.6 mg, 0.2 mmol). After 14 h the reaction mixture was poured into a water/ethyl acetate bilayer. The organic phase was concentrated and {3-[4-(2-oxo-2-phenyl-ethoxy)-phenyl]-isoxazol-4-yl}-carbamic acid tert-butyl ester (70 mg, 98%) was isolated from the resulting residue was purified by column chromatography.

Workup

  1. concentrationThe organic phase was concentrated

Sources & evidence

ORD record
ord-098b948051884fa383d0e85881468e11
Source dataset
uspto-grants-2016_03
Patent number
US09290465B2

Reaction notes

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