Ethanol → 2-Chloro-3-cyanobenzaldehyde

HRID 1377514Notes

Reaction equation

HRID 1377514 reaction equation
[Cl:1][C:2]1[C:10]([C:11]#[N:12])=[CH:9][CH:8]=[CH:7][C:3]=1[CH:4](Br)Br.[Cl-].[Na+].C([OH:17])C>O.[N+]([O-])([O-])=O.[Ag+]>[Cl:1][C:2]1[C:10]([C:11]#[N:12])=[CH:9][CH:8]=[CH:7][C:3]=1[CH:4]=[O:17]

Participants

6

Reactant 3

HCID 702Ethanol2×HCID 5234Sodium ChlorideHCID 229149372-Chloro-3-(dibromomethyl)benzonitrile

Product 1

HCID 119617032-Chloro-3-cyanobenzaldehyde

Reagents, catalysts & solvents 2

HCID 24470Silver NitrateCatalystHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

The crude product of the compound from Example II is dissolved in 1.5 l of 95% ethanol and warmed to 60° C. A solution of 186 g (1.1 mol) of silver nitrate in 380 ml of water which has been mixed with 750 ml of ethanol is rapidly added dropwise thereto at this temperature. After addition is complete, the mixture is subsequently stirred for one hour and then mixed with 50 ml of saturated sodium chloride solution. After cooling, the silver salts are filtered off and the filtrate is concentrated. The residue is taken up in methylene chloride and purified by filtration through a short silica gel column (eluent: dichloromethane). After concentrating the product fractions, 88 g (81%) of the title compound are obtained.

Workup

  1. additionis rapidly added dropwise
  2. additionAfter addition
  3. temperatureAfter cooling
  4. filtrationthe silver salts are filtered off
  5. concentrationthe filtrate is concentrated
  6. filtrationpurified by filtration through a short silica gel column (eluent: dichloromethane)
  7. concentrationAfter concentrating the product fractions, 88 g (81%) of the title compound
  8. customare obtained

Sources & evidence

ORD record
ord-85f4729a64664e61a81178957e65d87a
Source dataset
uspto-grants-1997_09
Patent number
US05665740

Reaction notes

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