Potassium Carbonate → HCID 15501042, compound

HRID 1360319Notes

Reaction equation

HRID 1360319 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Br:8])[CH:5]=[CH:4][C:3]=1[OH:9].Br[CH:11]([CH2:17]Br)[C:12]([O:14][CH2:15][CH3:16])=[O:13].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:15]([O:14][C:12]([CH:11]1[CH2:17][NH:1][C:2]2[CH:7]=[C:6]([Br:8])[CH:5]=[CH:4][C:3]=2[O:9]1)=[O:13])[CH3:16]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 97945Ethyl 2,3-dibromopropionateHCID 3518402-Amino-4-Bromophenol

Product 1

HCID 15501042HCID 15501042, compoundYield 78.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 2-amino-4-bromophenol (5.00 g, 26.6 mmol), ethyl 2,3-dibromopropionate (7.84 g, 29.2 mmol), and potassium carbonate (10.3 g, 81.8 mmol) in acetone (55 mL) was heated at reflux for 16 h. After evaporation of volatile material, the residue was partitioned between dichloromethane and water. The organic layer was washed with 1 M aq. sodium carbonate solution and brine, dried (MgSO4), and evaporated. Chromatography (SiO2, heptane-ethyl acetate gradient produced 6-bromo-3,4-dihydro-2H-benzo[1,4]oxazine-2-carboxylic acid ethyl ester (5.95 g, 78%). Orange solid, MS (ISP)=286.0 (M+H)+.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 16 h
  3. customAfter evaporation of volatile material
  4. customthe residue was partitioned between dichloromethane and water
  5. washThe organic layer was washed with 1 M aq. sodium carbonate solution and brine
  6. dry with materialdried (MgSO4)
  7. customevaporated

Sources & evidence

ORD record
ord-ee1c4ac4253a4dd684c36cde359a0d41
Source dataset
uspto-grants-2011_02
Patent number
US07879845B2

Reaction notes

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