Lithium Bromide → 4-(Bromomethyl)-2,2-dimethyloxane
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]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
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
- temperaturewas refluxed under nitrogen for 4 h
- temperatureto cool
- customthe solvent was evaporated
- additionThe residue was treated with saturated sodium bicarbonate solution
- extractionwas extracted with DCM (×3)
- washThe combined organics were washed with dilute brine
- customdried
- customevaporated
Sources & evidence
- ORD record
- ord-8ae74852c85d42b8b5654a2e2118480c
- Source dataset
- uspto-grants-2011_07
- Patent number
- US07977344B2
Reaction notes
Loading…