Hydrogen Peroxide → 4-(4'-Methoxy-biphenyl-4-yl)-5-methyl-2-(4-trifluoromethyl-phenyl)-oxazole

HRID 47656Notes

Reaction equation

HRID 47656 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1.Br[C:13]1[CH:18]=[CH:17][C:16]([C:19]2[N:20]=[C:21]([C:25]3[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=3)[O:22][C:23]=2[CH3:24])=[CH:15][CH:14]=1.C(=O)([O-])[O-].[Na+].[Na+].OO>C(O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O.C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:13]2[CH:14]=[CH:15][C:16]([C:19]3[N:20]=[C:21]([C:25]4[CH:26]=[CH:27][C:28]([C:31]([F:32])([F:34])[F:33])=[CH:29][CH:30]=4)[O:22][C:23]=3[CH3:24])=[CH:17][CH:18]=2)=[CH:5][CH:4]=1

Participants

9

Reactant 4

HCID 784Hydrogen PeroxideHCID 10340Sodium CarbonateHCID 201262(4-Methoxyphenyl)boronic acidHCID 106912782-[4-(Trifluoromethyl)phenyl]-4-(4-bromophenyl)-5-methyloxazole

Product 1

HCID 98016094-(4'-Methoxy-biphenyl-4-yl)-5-methyl-2-(4-trifluoromethyl-phenyl)-oxazoleYield 82.2%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

4-Methoxy-benzeneboronic acid (1.44 g, 7.19 mmol) in ethyl alcohol (5 mL) was added into a mixture of 4-(4-bromo-phenyl)-5-methyl-2-(4-trifluoromethyl-phenyl)-oxazole (2.5 g, 6.54 mmol), sodium carbonate (2N, 6.5 mL), tetrakis(triphenylphosphine)palladium(0) (0.23 g, 0.196 mmol), and toluene (200 mL). The reaction mixture was refluxed for 12 hours, cooled to room temperature, and treated with hydrogen peroxide (30%, 5 mL) for 1 hour. Then, the mixture was poured into water and extracted with ethyl acetate. The organic extracts were dried over MgSO4. Evaporation and crystallization from hexanes/ethyl ether gave a white solid (2.2 g, 82% yield): mp 167-168° C.; MS m/e 409 (M+);

Workup

  1. temperatureThe reaction mixture was refluxed for 12 hours
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic extracts were dried over MgSO4
  4. customEvaporation and crystallization from hexanes/ethyl ether

Sources & evidence

ORD record
ord-e0c7ff00a2bb40d1a7fb4b190f05e632
Source dataset
uspto-grants-2004_03
Patent number
US06699896B1

Reaction notes

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