(4-Bromophenyl)boronic acid → 4-(4-Bromo-phenyl)-3,5-dimethyl-isoxazole

HRID 858564Notes

Reaction equation

HRID 858564 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](B(O)O)=[CH:4][CH:3]=1.[CH3:11][C:12]1[C:16](I)=[C:15]([CH3:18])[O:14][N:13]=1.C([O-])(O)=O.[Na+]>COCCOC.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:16]2[C:12]([CH3:11])=[N:13][O:14][C:15]=2[CH3:18])=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 79599(4-Bromophenyl)boronic acidHCID 516892Sodium BicarbonateHCID 6138834-Iodo-3,5-dimethyl-1,2-oxazole

Product 1

HCID 103324224-(4-Bromo-phenyl)-3,5-dimethyl-isoxazoleYield 86%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 4-bromophenylboronic acid (1 g, 5 mmol), 3,5-dimethyl-4-iodoisoxazole (0.93 g, 4.2 mmol), bis(triphenylphospine)palladium(II) chloride (59 mg, 2 mol %), NaHCO3 (1.06 g, 12.6 mmol) in DME (5 mL) and H2O (5 mL) was heated to 80° C. under N2 for 18 h. The reaction mixture was partitioned between 1 N HCl and EtOAc. The organic layer was washed with saturated NaHCO3, brine, dried over Na2SO4 and concentrated. The residue was purified by silica gel chromatography (5% EtOAc in hexanes) to give the title compound as a white solid (0.9 g, 86%).

Workup

  1. customThe reaction mixture was partitioned between 1 N HCl and EtOAc
  2. washThe organic layer was washed with saturated NaHCO3, brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel chromatography (5% EtOAc in hexanes)

Sources & evidence

ORD record
ord-d3f30fc64a47480d858c810e9141ac7f
Source dataset
uspto-grants-2006_12
Patent number
US07148226B2

Reaction notes

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