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

HRID 1637239Notes

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

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. 1H NMR (CDCl3) 67 4.4 (s, 2 H), 2.25 (s, 3 H), 2.05 (s, 3 H).

Workup

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

Sources & evidence

ORD record: ord-9aa13072031848c591ff82be78d222b2
Source dataset: uspto-grants-2000_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06040321

Reaction notes

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