Sodium Methoxide → 5-(4-Bromo-2-methoxyphenyl)-2-methyloxazole

HRID 71209Notes

Reaction equation

HRID 71209 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][C:11]([CH3:13])=[N:10][CH:9]=2)=[C:4](F)[CH:3]=1.[CH3:15][O-:16].[Na+]>CN(C=O)C.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][C:11]([CH3:13])=[N:10][CH:9]=2)=[C:4]([O:16][CH3:15])[CH:3]=1

Participants

5

Reactant 2

HCID 10942334Sodium MethoxideHCID 666082265-(4-Bromo-2-fluorophenyl)-2-methyloxazole

Product 1

HCID 666087325-(4-Bromo-2-methoxyphenyl)-2-methyloxazoleYield 99.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of 5-(4-bromo-2-fluorophenyl)-2-methyl-1,3-oxazole (10 g) in DMF (80 mL) was added sodium methoxide (28% methanol solution, 11.3 g) at 0° C., and the mixture was stirred at 80° C. for 2 hr under a nitrogen atmosphere. The reaction mixture was cooled to 0° C., and diluted with water, and the resultant solid was collected by filtration to give the title compound (10.4 g).

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. filtrationthe resultant solid was collected by filtration

Sources & evidence

ORD record
ord-c0e5e71cbb594082ad0409a94949facd
Source dataset
uspto-grants-2014_09
Patent number
US08822699B2

Reaction notes

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