Potassium Carbonate → 7-Bromo-2,2-dimethyl-2H-benzo[b][1,4]oxazin-3(4H)-one

HRID 1842039Notes

Reaction equation

HRID 1842039 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][C:3]=1[OH:9].C(=O)([O-])[O-].[K+].[K+].C([O:18][C:19](=O)[C:20](Br)([CH3:22])[CH3:21])C>CC(C)=O>[Br:8][C:5]1[CH:6]=[CH:7][C:2]2[NH:1][C:19](=[O:18])[C:20]([CH3:22])([CH3:21])[O:9][C:3]=2[CH:4]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl esterHCID 143206052-Amino-5-bromophenol

Product 1

HCID 670173227-Bromo-2,2-dimethyl-2H-benzo[b][1,4]oxazin-3(4H)-oneYield 67.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

5.0 g 2-Amino-5-bromophenol were dissolved in 100 ml acetone. Then 11.0 g potassium carbonate and 6.74 g ethyl-2-bromoisobutyrate were added. The reaction mixture was stirred at room temperature overnight and refluxed overnight. The cooled reaction mixture was then filtrated and the filtrate concentrated in vacuo. The resulting residue was purified by chromatography on silica gel to obtain 4.6 g 7-Bromo-2,2-dimethyl-4H-benzo[1,4]oxazin-3-one as a yellow solid.

Workup

  1. temperaturerefluxed overnight
  2. customThe cooled reaction mixture
  3. filtrationwas then filtrated
  4. concentrationthe filtrate concentrated in vacuo
  5. customThe resulting residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-4d41c692221c426bb56613fa5b161538
Source dataset
uspto-grants-2015_02
Patent number
US08946212B2

Reaction notes

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