Benzoyl Peroxide → 2-(Bromomethyl)-4,5-dimethyl-1,3-oxazole

HRID 1060246Notes

Reaction equation

HRID 1060246 reaction equation
[CH3:1][C:2]1[O:3][C:4]([CH3:8])=[C:5]([CH3:7])[N:6]=1.[Br:9]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:9][CH2:1][C:2]1[O:3][C:4]([CH3:8])=[C:5]([CH3:7])[N:6]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 302152,4,5-TrimethyloxazoleHCID 67184N-bromobutanimide

Product 1

HCID 118302042-(Bromomethyl)-4,5-dimethyl-1,3-oxazoleYield 7.8%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
76 °C

Procedure

A mixture of 2,4,5-trimethyloxazole (0.50 mL, 4.3 mmol), N-bromosuccinimide (0.77 g, 4.3 mmol) and benzoyl peroxide (0.21 g, 0.86 mmol) in carbon tetrachloride (4 mL) was heated at 76° C. under nitrogen atm.for 3 hrs. After cooling to rt, the solid was removed by filtration. The filtrate solution was washed with saturated aqueous NaHCO3 (20 mL) and concentrated. The residue was purified by flash column chromatography (SiO2; hexanes:ethyl acetate/4:1) to afford 2-(bromomethyl)-4,5-dimethyloxazole (64 mg) as an yellow oil.

Workup

  1. temperatureAfter cooling to rt
  2. customthe solid was removed by filtration
  3. washThe filtrate solution was washed with saturated aqueous NaHCO3 (20 mL)
  4. concentrationconcentrated
  5. customThe residue was purified by flash column chromatography (SiO2; hexanes:ethyl acetate/4:1)

Sources & evidence

ORD record
ord-c8974f433eff4352a47aa974841e7ad2
Source dataset
uspto-grants-2003_02
Patent number
US06521759B2

Reaction notes

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