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

HRID 1385191Notes

Reaction equation

HRID 1385191 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-6fd5813e7f274bedb8cdf8ce6545bc3d
Source dataset
uspto-grants-2001_07
Patent number
US06262096B1

Reaction notes

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