Carbon tetrabromide → tert-Butyl 3-bromopropionate
Reaction equation
[C:1]([O:5][C:6](=[O:10])[CH2:7][CH2:8]O)([CH3:4])([CH3:3])[CH3:2].C(Br)(Br)(Br)[Br:12].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(#N)C>[C:1]([O:5][C:6](=[O:10])[CH2:7][CH2:8][Br:12])([CH3:4])([CH3:3])[CH3:2]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
3-Hydroxy-propionic acid tert-butyl ester is dissolved in acetonitrile and carbon tetrabromide and triphenylphosphine is added. The mixture is stirred at room temperature overnight. After this time the mixture is concentrated in vacuo. The gummy solid is triturated with hexanes and the liquid decanted, passed through pad of silica to remove any triphenylphosphine oxide, and concentrated in vacuo. 1H NMR (400 MHz, CHLOROFORM-d) ppm 1.3 (9H, s), 2.06-2.27 (2H, m), 4.07-4.25 (2H, m).
Workup
- concentrationAfter this time the mixture is concentrated in vacuo
- customThe gummy solid is triturated with hexanes
- customthe liquid decanted
- customto remove any triphenylphosphine oxide
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-dcb257f0551e46a2852671ecd9f8e2c7
- Source dataset
- uspto-grants-2014_01
- Patent number
- US08629157B2
Reaction notes
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