Bromine → 2-Bromo-1-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethan-1-one

HRID 4403

Reaction equation

[C:1]([C:4]1[N:5]=[C:6]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[O:7][C:8]=1[CH3:9])(=[O:3])[CH3:2].[Br:16]Br.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[Br:16][CH2:2][C:1]([C:4]1[N:5]=[C:6]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[O:7][C:8]=1[CH3:9])=[O:3]

Participants

Conditions

Temperature: 55 °C

Procedure

To a stirred solution of 4-acetyl-5-methyl-2-phenyloxazole (12.0 g) in chloroform (100 ml) was added at 50° C. a solution of bromine (10.5 g) in chloroform (10 ml). The mixture was further heated at 55° C. for 30 minutes and poured into saturated aqueous sodium bicarbonate solution (500 ml). The chloroform layer was separated and the aqueous layer was extracted with chloroform. The conbined chloroform layer was washed with water and dried (MgSO4). Evaporation of the solvent gave 4-bromoacetyl-5-methyl-2-phenyloxazole as crystals (14.5 g, 86.3%). Recrystallization from ethyl ether-hexane gave colorless rods, mp 88°-89° C.

Workup

customThe chloroform layer was separated
extractionthe aqueous layer was extracted with chloroform
washThe conbined chloroform layer was washed with water
dry with materialdried (MgSO4)
customEvaporation of the solvent

Sources & evidence

ORD record: ord-fa6b00b25d154a97988b043a2abfac3a
Source dataset: uspto-grants-1988_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04725610

Linked notes

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