Ethyl Bromide → Triethyl 4-phosphonocrotonate, mixture of isomers

HRID 333040Notes

Reaction equation

HRID 333040 reaction equation
Br[CH2:2]/[CH:3]=[CH:4]/[C:5]([O:7][CH2:8][CH3:9])=[O:6].[CH2:10]([O:12][P:13]([O:17]CC)[O:14][CH2:15][CH3:16])[CH3:11].C(Br)C>>[CH3:9][CH2:8][O:7][C:5](/[CH:4]=[CH:3]/[CH2:2][P:13]([O:14][CH2:15][CH3:16])([O:12][CH2:10][CH3:11])=[O:17])=[O:6]

Participants

4

Reactant 3

HCID 6332Ethyl BromideHCID 31215Triethyl phosphiteHCID 5373944Ethyl (E)-4-bromobut-2-enoate

Product 1

HCID 5365783Triethyl 4-phosphonocrotonate, mixture of isomers

Procedure

Ethyl 4-bromocrotonate (7.0 mL) was added to triethylphosphite (9.9 mL) at 120 to 130° C. during 60 minutes periods. After the generation of ethyl bromide ceased, the reaction solution was stirred at the same temperature for 3 hours. After cooling, the resulting reaction solution was concentrated under reduced pressure. Then the residue was purified by distillation at 150 to 210° C. under reduced pressure (17 to 21 hPa) to give triethyl 4-phosphonocrotonate as colorless oil.

Workup

  1. temperatureAfter cooling
  2. customthe resulting reaction solution
  3. concentrationwas concentrated under reduced pressure
  4. distillationThen the residue was purified by distillation at 150 to 210° C. under reduced pressure (17 to 21 hPa)

Sources & evidence

ORD record
ord-1b7724c1078e4691bfc77b728110268c
Source dataset
uspto-grants-2014_11
Patent number
US08877953B2

Reaction notes

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