Benzoyl Peroxide → HCID 12748355, compound

HRID 915667Notes

Reaction equation

HRID 915667 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][CH:3]=1.[Br:13]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:13][CH2:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)=[N:4][CH:3]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 2478295-Methyl-2-phenyloxazole

Product 1

HCID 12748355HCID 12748355, compoundYield 98.9%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

Prepare a solution of 5-methyl-2-phenyloxazole (790 mg, 4.97 mmol) in CCl4 (70 mL) under nitrogen. Add N-bromosuccinimide (884 mg, 4.97 mmol) and a catalytic amount of benzoyl peroxide. Reflux the mixture for 2 hours, cool to room temperature, and stir overnight. Wash the reaction mixture with a saturated solution of Na2SO3 (75 mL) followed by saturated sodium hydrogencarbonate (100 mL). Dry the organic phase (magnesium sulfate), filter, and concentrate to afford 1.17 g of 5-bromomethyl-2-phenyloxazole as a white solid. MS: m/e=238 (MH+)

Workup

  1. temperatureReflux the mixture for 2 hours
  2. washWash the reaction mixture with a saturated solution of Na2SO3 (75 mL)
  3. dry with materialDry the organic phase (magnesium sulfate)
  4. filtrationfilter
  5. concentrationconcentrate

Sources & evidence

ORD record
ord-f8c4ea6b339a41c2819e70757f3dae64
Source dataset
uspto-grants-2007_09
Patent number
US07265246B2

Reaction notes

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