1,3-Dibromo-2-propanol → 2-(2-bromo-1-(bromomethyl)ethoxy)tetrahydro-2H-pyran

HRID 1725505Notes

Reaction equation

HRID 1725505 reaction equation
[Br:1][CH2:2][CH:3]([OH:6])[CH2:4][Br:5].[O:7]1[CH:12]=[CH:11][CH2:10][CH2:9][CH2:8]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(Cl)(Cl)Cl>[Br:1][CH2:2][CH:3]([CH2:4][Br:5])[O:6][CH:8]1[CH2:9][CH2:10][CH2:11][CH2:12][O:7]1

Participants

5

Reactant 3

HCID 72871,3-Dibromo-2-propanolHCID 80803,4-dihydro-2H-pyranHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 116236072-(2-bromo-1-(bromomethyl)ethoxy)tetrahydro-2H-pyran

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a mixture of 10 g of 1,3-dibromopropan-2-ol, 5.0 ml of 3,4-dihydro-2H-pyran and 50 ml of chloroform was added a catalytic amount of p-toluenesulfonic acid monohydrate followed by stirring at room temperature for 3 hours. The reaction solution was concentrated, diluted with diethyl ether and washed with saturated sodium bicarbonate and brine. The resulting organic layer was dried over magnesium sulfate and filtered, and the filtrate was concentrated to give the title compound.

Workup

  1. concentrationThe reaction solution was concentrated
  2. additiondiluted with diethyl ether
  3. washwashed with saturated sodium bicarbonate and brine
  4. dry with materialThe resulting organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-d65639a1b0034a7c8bdaf7922beb54b4
Source dataset
uspto-grants-2009_02
Patent number
US07491720B2

Reaction notes

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