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

HRID 1172449Notes

Reaction equation

HRID 1172449 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-e4cd6d9310d74bccbd04071bffa0acb4
Source dataset
uspto-grants-2010_11
Patent number
US07834018B2

Reaction notes

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