Potassium Carbonate → HCID 21702633, compound

HRID 1596722Notes

Reaction equation

HRID 1596722 reaction equation
[Br:1][C:2]1[CH:11]=[C:6]([C:7]([O:9][CH3:10])=[O:8])[C:5]([OH:12])=[CH:4][CH:3]=1.Br[CH:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH3:15].C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:12][CH:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH3:15])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11454(1-Bromoethyl)benzeneHCID 77683Methyl 5-bromosalicylate

Product 1

HCID 21702633HCID 21702633, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of methyl 5-bromosalicylate (12.70 g, 55 mmol), (1-bromoethyl)benzene (7.05 mL, 50 mmol), and K2CO3 (20.73 g, 150 mmol) in acetone (250 mL) is refluxed 18 hours. The mixture is then filtered and the filtrate is concentrated in vacuo. The residue is dissolved in EtOAc (250 mL) and then washed with 1 N NaOH (2×150 mL) and brine (1×100 mL), and dried over MgSO4. Concentration in vacuo yields methyl 5-bromo-2-(1-phenylethoxy)-benzoate.

Workup

  1. filtrationThe mixture is then filtered
  2. concentrationthe filtrate is concentrated in vacuo
  3. dissolutionThe residue is dissolved in EtOAc (250 mL)
  4. washwashed with 1 N NaOH (2×150 mL) and brine (1×100 mL)
  5. dry with materialdried over MgSO4
  6. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-82d05ec75ad749b9a899f80b6375ff70
Source dataset
uspto-grants-2001_09
Patent number
US06291530B1

Reaction notes

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