Lithium Bromide → 4-(Bromomethyl)-2,2-dimethyloxane

HRID 1010987Notes

Reaction equation

HRID 1010987 reaction equation
CS(O[CH2:6][CH:7]1[CH2:12][CH2:11][O:10][C:9]([CH3:14])([CH3:13])[CH2:8]1)(=O)=O.[Br-:15].[Li+]>CC(C)=O>[Br:15][CH2:6][CH:7]1[CH2:12][CH2:11][O:10][C:9]([CH3:14])([CH3:13])[CH2:8]1

Participants

4

Reactant 2

HCID 82050Lithium BromideHCID 57699693(2,2-Dimethyltetrahydro-2H-pyran-4-yl)methyl methanesulfonate

Product 1

HCID 576996994-(Bromomethyl)-2,2-dimethyloxaneYield 88%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of (2,2-dimethyltetrahydro-2H-pyran-4-yl)methyl methanesulfonate (1.5 g) and anhydrous lithium bromide (2.72 g) in acetone (40 mL) was refluxed under nitrogen for 4 h. The reaction was allowed to cool and the solvent was evaporated. The residue was treated with saturated sodium bicarbonate solution and was extracted with DCM (×3). The combined organics were washed with dilute brine, dried by passing through a hydrophobic frit and evaporated to give the title compound as a brown oil (1.23 g).

Workup

  1. temperaturewas refluxed under nitrogen for 4 h
  2. temperatureto cool
  3. customthe solvent was evaporated
  4. additionThe residue was treated with saturated sodium bicarbonate solution
  5. extractionwas extracted with DCM (×3)
  6. washThe combined organics were washed with dilute brine
  7. customdried
  8. customevaporated

Sources & evidence

ORD record
ord-8ae74852c85d42b8b5654a2e2118480c
Source dataset
uspto-grants-2011_07
Patent number
US07977344B2

Reaction notes

Loading…