Hydrochloric Acid → HCID 54225767, compound

HRID 638002Notes

Reaction equation

HRID 638002 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[C:5]1[CH:10]=[C:9](Br)[C:8]([Cl:12])=[CH:7][C:6]=1[O:13][CH3:14])[CH3:2].[Cu][C:17]#[N:18].CN(C)C=O.Cl>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:15])[C:5]1[CH:10]=[C:9]([C:17]#[N:18])[C:8]([Cl:12])=[CH:7][C:6]=1[O:13][CH3:14])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 50879134HCID 50879134, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 54225767HCID 54225767, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

14.7 g (0.05 mol) of 5-bromo-4-chloro-2-methoxybenzoic acid ethyl ester, 5.4 g (0.06 mol) of copper(I) cyanide and 8 ml of dimethylformamide are heated at 190° for three hours while stirring under a nitrogen atmosphere. After cooling, the reaction mixture is stirred well with 250 ml of methylene chloride and 250 ml of 2N hydrochloric acid. The insoluble portions are filtered off with suction and the layers are separated in a separating funnel. The methylene chloride solution is washed neutral with water and then concentrated by evaporation. 4-Chloro-5-cyano-2-methoxybenzoic acid ethyl ester is obtained as residue which, after recrystallisation from methylene chloride/hexane, melts at 102°-103°.

Workup

  1. temperatureAfter cooling
  2. filtrationThe insoluble portions are filtered off with suction
  3. customthe layers are separated in a separating funnel
  4. washThe methylene chloride solution is washed neutral with water
  5. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-fea901b574fc4ef293852d5e5137b167
Source dataset
uspto-grants-1985_12
Patent number
US04559349

Reaction notes

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