Hydrochloric Acid → 3-Bromo-4-(4-trifluoromethyl-benzyl)-4H-thieno[3,2-b]pyrrole

HRID 1951645Notes

Reaction equation

HRID 1951645 reaction equation
[Br:1][C:2]1[C:6]2[N:7]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=3)[C:8](C(O)=O)=[CH:9][C:5]=2[S:4][CH:3]=1.Cl>N1C2C(=CC=CC=2)C=CC=1.[Cu]>[Br:1][C:2]1[C:6]2[N:7]([CH2:13][C:14]3[CH:15]=[CH:16][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:18][CH:19]=3)[CH:8]=[CH:9][C:5]=2[S:4][CH:3]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 582976983-Bromo-4-(4-trifluoromethyl-benzyl)-4H-thieno[3,2-b]pyrrole-5-carboxylic acid

Product 1

HCID 582976723-Bromo-4-(4-trifluoromethyl-benzyl)-4H-thieno[3,2-b]pyrroleYield 82.3%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 7047QuinolineSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 3 g of the product of Step 4 and 0.3 g of copper powder in 50 ml of quinoline was heated in oil bath at 140° C. for 4 h. The reaction mixture was cooled and acidified with 6 N HCl and then extracted with 150 ml of ether. The ether layer was washed with 200 ml of 2 N HCl, dried over Na2SO4, filtered, and concentrated to give 2.2 g of the title compound as a light brown solid.

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with 150 ml of ether
  3. washThe ether layer was washed with 200 ml of 2 N HCl
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b65f395fb4f64c30bd70efb3bc786c11
Source dataset
uspto-grants-2013_03
Patent number
US08404736B2

Reaction notes

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