3,4-dihydro-2H-pyran → 2-[(2-Bromophenyl)methoxy]oxane

HRID 342173Notes

Reaction equation

HRID 342173 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][OH:5].[O:10]1[CH:15]=[CH:14][CH2:13][CH2:12][CH2:11]1.C(=O)(O)[O-].[Na+]>ClCCl.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>[Br:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][O:5][CH:11]1[CH2:12][CH2:13][CH2:14][CH2:15][O:10]1

Participants

6

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 728502-Bromobenzyl alcoholHCID 516892Sodium Bicarbonate

Product 1

HCID 53150262-[(2-Bromophenyl)methoxy]oxaneYield 99.3%

Reagents, catalysts & solvents 2

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

Procedure

Pyridinium p-toluenesulfonate (0.30 g, 0.0012 mol) was added to a solution of 2-bromobenzyl alcohol (25 g, 0.134 mol) in dichloromethane (100 ml), and the mixture was stirred at room temperature. To this mixture was added 3,4-dihydro-2H-pyrane (16.86 g, 0.20 mol). After the resulting mixture was stirred at room temperature for 2 hours, a saturated aqueous solution (200 ml) of sodium bicarbonate was added. The mixture was extracted with dichloromethane (200 ml). After the mixture was dried over anhydrous magnesium sulfate, the solvent was evaporated to obtain the desired compound 1-bromo-2-(2-tetrahydropyranyloxymethyl)benzene (36.00 g, Yield: 99.3%) as an oil.

Workup

  1. stirringAfter the resulting mixture was stirred at room temperature for 2 hours
  2. extractionThe mixture was extracted with dichloromethane (200 ml)
  3. dry with materialAfter the mixture was dried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-868af12e0a884703b7c9e51f5b0bf836
Source dataset
uspto-grants-1999_01
Patent number
US05856573

Reaction notes

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