Bromobenzene → HCID 13837941, compound

HRID 653157Notes

Reaction equation

HRID 653157 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([C:12]([OH:14])=[O:13])=[CH:6]2.Br[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[OH-].[K+]>CN(C)C=O.[Cu]=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:7]([C:12]([OH:14])=[O:13])=[CH:6]2

Participants

6

Reactant 3

HCID 7961BromobenzeneHCID 14797Potassium HydroxideHCID 204015-Methoxyindole-2-carboxylic acid

Product 1

HCID 13837941HCID 13837941, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 14829Copper oxideCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 60.0 g (0.32 mole) of 5-methoxy-1H-indole-2-carboxylic acid, 35.0 ml (52.2 g; 0.32 mole) of bromobenzene, 36.0 g (0.64 mole) of potassium hydroxide, and 10.0 g (0.13 mole) of copper (II) oxide in 750 ml of N,N-dimethylformamide was stirred and heated at reflux under a nitrogen atmosphere for six hours. The cooled reaction mixture was added to 1.5 kg of ice/water and filtered through a bed of Celite filter-aid. Acidification of the filtrate with dilute hydrochloric acid precipitated the product. The solid was filtered and washed with water to yield 83.0 g (95% yield) of crude acid product. A sample recrystallized from ether/hexane was analytically pure, mp 197°-204° C.

Workup

  1. temperatureheated
  2. temperatureat reflux under a nitrogen atmosphere for six hours
  3. customThe cooled reaction mixture
  4. filtrationfiltered through a bed of Celite
  5. filtrationfilter-aid
  6. customAcidification of the filtrate with dilute hydrochloric acid precipitated the product
  7. filtrationThe solid was filtered
  8. washwashed with water

Sources & evidence

ORD record
ord-f1b71b09990b49db9d64c2c0b76a1e20
Source dataset
uspto-grants-1987_06
Patent number
US04675332

Reaction notes

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