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

HRID 4403
Notes
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Reaction equation

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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 24408BromineHCID 516892Sodium BicarbonateHCID 123378491-(5-Methyl-2-phenyl-1,3-oxazol-4-yl)ethan-1-one

Product 1

HCID 149136502-Bromo-1-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethan-1-oneYield 86.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

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

  1. customThe chloroform layer was separated
  2. extractionthe aqueous layer was extracted with chloroform
  3. washThe conbined chloroform layer was washed with water
  4. dry with materialdried (MgSO4)
  5. 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

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes