Pyridine → 2-Bromo-1,1,1-triethoxypropane

HRID 2295526Notes

Reaction equation

HRID 2295526 reaction equation
[C:1]([O:10][CH2:11][CH3:12])([O:7][CH2:8][CH3:9])([O:4][CH2:5][CH3:6])[CH2:2][CH3:3].N1C=CC=CC=1.[Br:19]Br>C(Cl)(Cl)(Cl)Cl>[CH2:11]([O:10][C:1]([O:4][CH2:5][CH3:6])([O:7][CH2:8][CH3:9])[CH:2]([Br:19])[CH3:3])[CH3:12]

Participants

5

Reactant 3

HCID 1049PyridineHCID 24408BromineHCID 66995Ethyl orthopropionate

Product 1

HCID 27792852-Bromo-1,1,1-triethoxypropaneYield 81%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of 176 g (1 mole) of triethyl orthopropionate and 96 g (1.2 moles) of pyridine in 1 l of carbon tetrachloride was placed in a 2 l flask and 160 g (1 mole) of bromine was slowly added over two hours to the solution under ice-cooling. The resultant reaction mixture was allowed to stand at room temperature for one day to form a precipitate, which was then filtered off. The filtrate was concentrated by evaporation of the solvent and the residue was subjected to distillation under reduced pressure to afford 206 g (81%) of 1,1,1-triethoxy-2-bromopropane with a boiling point of 85° C./13 mmHg.

Workup

  1. temperaturecooling
  2. customThe resultant reaction mixture
  3. customto form a precipitate, which
  4. filtrationwas then filtered off
  5. concentrationThe filtrate was concentrated by evaporation of the solvent
  6. distillationthe residue was subjected to distillation under reduced pressure

Sources & evidence

ORD record
ord-9fa1efd560ff4003a47342236a8d546b
Source dataset
uspto-grants-1984_01
Patent number
US04425473

Reaction notes

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