p-Toluenesulfonic acid → 2-Bromo-5-(2-tetrahydropyranyloxy)pyridine

HRID 15037

Reaction equation

HRID 15037 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][N:3]=1.[O:9]1[CH:14]=[CH:13][CH2:12][CH2:11][CH2:10]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>ClCCl.C(Cl)(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH:10]2[CH2:11][CH2:12][CH2:13][CH2:14][O:9]2)=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 27628652-Bromo-5-hydroxypyridine

Product 1

HCID 866148912-Bromo-5-(2-tetrahydropyranyloxy)pyridineYield 55%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-bromo-5-hydroxypyridine (1.0 g, 5.75 mmols), 3,4-dihydro-2H-pyran (0.80 mL, 8.77 mmols) and p-toluenesulfonic acid (110 mg, 0.578 mmol) was stirred overnight in dichloromethane (20 mL) at room temperature. The reaction liquid was diluted with chloroform, washed with saturated brine and dried over anhydrous magnesium sulfate. Concentrating the solvent under reduced pressure, the resulting residue was purified on silica gel column chromatography (C-300; ethyl acetate:hexane=1:20-1:10) to provide the title compound (0.81 g, 55%).

Workup

  1. customThe reaction liquid
  2. washwashed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationConcentrating the solvent under reduced pressure
  5. customthe resulting residue was purified on silica gel column chromatography (C-300; ethyl acetate:hexane=1:20-1:10)

Sources & evidence

ORD record
ord-22d50e01a3bc4b4d88cece5f10779ccd
Source dataset
uspto-grants-2010_06
Patent number
US07732456B2

Linked notes

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