Carbon Dioxide → Ethyl 4-(2-bromoethoxy)benzoate

HRID 839842Notes

Reaction equation

HRID 839842 reaction equation
[Br:1][CH2:2][CH2:3][O:4][C:5]1[CH:12]=[CH:11][C:8]([C:9]#N)=[CH:7][CH:6]=1.Cl.N=O.C([O-])(O)=[O:17].[Na+].C(=O)=O.[CH3:24][CH2:25][O:26]CC>C(O)C.O.CCOCC>[CH2:25]([O:26][C:9](=[O:17])[C:8]1[CH:11]=[CH:12][C:5]([O:4][CH2:3][CH2:2][Br:1])=[CH:6][CH:7]=1)[CH3:24]

Participants

9

Reactant 6

HCID 280Carbon DioxideHCID 313Hydrochloric Acid2×HCID 945NitroxylHCID 3283Diethyl EtherHCID 516892Sodium BicarbonateHCID 24522124-(2-Bromoethoxy)benzonitrile

Product 1

HCID 12708668Ethyl 4-(2-bromoethoxy)benzoate

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 21584184Diethylether waterSolvent

Procedure

A solution of 68 g of 4-(2-bromethoxy)-benzonitrile in 500 ml of absolute ether and 50 ml of absolute ethanol was saturated with dry hydrogen chloride while cooling with ice. After standing for three days in the refrigerator the precipitated hydrochloride of the imino ether was suctionfiltered, suspended in water/ether and NaHCO3 was added while stirring until the development of CO2 was finished. The organic phase was dried with MgSO4 and the solvent was evaporated under reduced pressure. 100 ml of absolute ethanol and 3 ml of concentrated sulfuric acid were added to the residue and the whole was heated to the boiling point for 1 hour.

Workup

  1. temperaturewhile cooling with ice
  2. dry with materialThe organic phase was dried with MgSO4
  3. customthe solvent was evaporated under reduced pressure
  4. addition100 ml of absolute ethanol and 3 ml of concentrated sulfuric acid were added to the residue
  5. temperaturethe whole was heated to the boiling point for 1 hour

Sources & evidence

ORD record
ord-a34cba2c7c904c83857c60bcbcf104d3
Source dataset
uspto-grants-1978_06
Patent number
US04097496

Reaction notes

Loading…