Carbon tetrabromide → tert-Butyl 3-bromopropionate

HRID 469718

Reaction equation

HRID 469718 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

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 16218743tert-Butyl 3-hydroxypropanoate

Product 1

HCID 256128tert-Butyl 3-bromopropionate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

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

  1. concentrationAfter this time the mixture is concentrated in vacuo
  2. customThe gummy solid is triturated with hexanes
  3. customthe liquid decanted
  4. customto remove any triphenylphosphine oxide
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-dcb257f0551e46a2852671ecd9f8e2c7
Source dataset
uspto-grants-2014_01
Patent number
US08629157B2

Linked notes

Loading…