1-Bromo-2-Chloroethane → HCID 59457508, compound

HRID 1710759Notes

Reaction equation

HRID 1710759 reaction equation
[CH3:1][O:2][C:3](=[O:17])[CH2:4][C:5]1[N:6]=[C:7]([C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)[O:8][CH:9]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:25][CH2:26][Cl:27]>CC(C)=O>[Cl:27][CH2:26][CH2:25][O:16][C:13]1[CH:14]=[CH:15][C:10]([C:7]2[O:8][CH:9]=[C:5]([CH2:4][C:3]([O:2][CH3:1])=[O:17])[N:6]=2)=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 78491-Bromo-2-ChloroethaneHCID 11430Potassium CarbonateHCID 136046543HCID 136046543, compound

Product 1

HCID 59457508HCID 59457508, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of methyl[2-(4-hydroxyphenyl)-1,3-oxazol-4-yl]acetate 150 (1 g, 4.29 mmol, 1 eq), potassium carbonate (2.37 g, 17.16 mmol, 4 eq) and 1-bromo-2-chloroethane (1.54 g, 10.7 mmol, 2.5 eq) in acetone (50 ml) is stirred at reflux for 140 h. Potassium carbonate is then filtered off and the solvent is evaporated. The residue is taken up in ethyl acetate and washed two times with an aqueous solution of sodium hydrogenocarbonate. The organic layer is dried over magnesium sulfate, filtered and concentrated under vacuum to give 1.1 g of methyl {2-[4-(2-chloroethoxy)phenyl]-1,3-oxazol-4-yl}acetate i51.

Workup

  1. temperatureat reflux for 140 h
  2. filtrationPotassium carbonate is then filtered off
  3. customthe solvent is evaporated
  4. washwashed two times with an aqueous solution of sodium hydrogenocarbonate
  5. dry with materialThe organic layer is dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-3744c1a459c74522b2b7b57b04894e91
Source dataset
uspto-grants-2010_09
Patent number
US07790720B2

Reaction notes

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