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

HRID 273367

Reaction equation

HRID 273367 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 hrs. 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-0b72634dd7964a618505719e779f1f36
Source dataset
uspto-grants-2008_11
Patent number
US07456218B2

Linked notes

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