Chloroform → 2-(4-bromo-2-methoxyphenoxy)tetrahydro-2H-pyran

HRID 15062

Reaction equation

HRID 15062 reaction equation
[O:1]1[CH:6]=[CH:5][CH2:4][CH2:3][CH2:2]1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.C(Cl)(Cl)Cl.[Br:28][C:29]1[CH:34]=[CH:33][C:32]([OH:35])=[C:31]([O:36][CH3:37])[CH:30]=1>[Cl-].[Na+].O>[Br:28][C:29]1[CH:34]=[CH:33][C:32]([O:35][CH:6]2[CH2:5][CH2:4][CH2:3][CH2:2][O:1]2)=[C:31]([O:36][CH3:37])[CH:30]=1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 80803,4-dihydro-2H-pyranHCID 2622344-Bromo-2-methoxyphenolHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)

Product 1

HCID 684306542-(4-bromo-2-methoxyphenoxy)tetrahydro-2H-pyranYield 86%

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

3,4-Dihydro-2H-pyran (2.0 mL) and pyridinium p-toluenesulfonate (370 mg) were added to chloroform solution (30 mL) of 4-bromo-2-methoxyphenol (3.0 g) and stirred at room temperature for 12 hours. Saturated brine was added to the reaction liquid, followed by extraction with chloroform. The organic layer was washed with water and dried over anhydrous magnesium sulfate. Concentrating the solvent under reduced pressure, the residue was purified on silica gel column chromatography (C-200; ethyl acetate:hexane=1:19) to provide the title compound (3.64 g, 86%).

Workup

  1. extractionfollowed by extraction with chloroform
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationConcentrating the solvent under reduced pressure
  5. customthe residue was purified on silica gel column chromatography (C-200; ethyl acetate:hexane=1:19)

Sources & evidence

ORD record
ord-bbb5dbd2e2ab41958523662e95cd9384
Source dataset
uspto-grants-2010_06
Patent number
US07732456B2

Linked notes

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