Water → (S)-(+)-1-Acetoxy-3-bromo-2-methyl-propane
Reaction equation
[Br:1][CH2:2][C@@H:3]([CH3:6])[CH2:4][OH:5].[C:7](OC(=O)C)(=[O:9])[CH3:8].O.C(OCC)(=O)C>N1C=CC=CC=1>[C:7]([O:5][CH2:4][C@H:3]([CH3:6])[CH2:2][Br:1])(=[O:9])[CH3:8]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
5 g of (S)-(+)-3-bromo-2-methyl-1-propanol (32.6 mmol) were stirred in 5 ml of pyridine at room temperature. 3.67 g of acetic anhydride (35.9 mmol) were added and the reaction mixture was stirred for 3 h at 70° C. Stirring was continued for 16 h at room temperature. 30 ml of water and 40 ml of ethyl acetate were added. The organic layer was separated and washed with a further portion of water, then dried over magnesium sulfate, filtered, and evaporated under reduced pressure, whereby 4.34 g of the title compound were obtained.
Workup
- stirringStirring
- waitwas continued for 16 h at room temperature
- customThe organic layer was separated
- washwashed with a further portion of water
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- customevaporated under reduced pressure
Sources & evidence
- ORD record
- ord-11aa72148de94870880eb1a437376a8e
- Source dataset
- uspto-grants-2012_06
- Patent number
- US08202868B2
Reaction notes
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