3,4-dihydro-2H-pyran → 2-(4-bromo-3-methylphenoxy)tetrahydro-2H-pyran

HRID 1163300Notes

Reaction equation

HRID 1163300 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[CH3:9].[O:10]1[CH:15]=[CH:14][CH2:13][CH2:12][CH2:11]1>ClCCl.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH:11]2[CH2:12][CH2:13][CH2:14][CH2:15][O:10]2)=[CH:4][C:3]=1[CH3:9]

Participants

5

Reactant 2

HCID 80803,4-dihydro-2H-pyranHCID 728574-Bromo-m-cresol

Product 1

HCID 231118382-(4-bromo-3-methylphenoxy)tetrahydro-2H-pyranYield 104.1%

Reagents, catalysts & solvents 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)CatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 4-bromo-3-methylphenol (4.72 g, 25.2 mmol), 3,4-dihydro-2H-pyran (3.18 g, 37.8 mmol) and pyridinium p-toluenesulfonate (0.628 g, 2.50 mmol) in dichloromethane (100 mL) was stirred at room temperature for 24 hr. The reaction mixture was washed with water and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give the title compound (7.11 g, including unreacted 3,4-dihydro-2H-pyran) as a yellow oil.

Workup

  1. washThe reaction mixture was washed with water
  2. dry with materialdried over anhydrous sodium sulfate
  3. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-76e39213654f4f4c9258d92342410c5e
Source dataset
uspto-grants-2010_10
Patent number
US07820837B2

Reaction notes

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