Hydrochloric Acid → 2-[(5-bromo-2-thienyl)carbonyl]benzenecarboxylic acid

HRID 2211103Notes

Reaction equation

HRID 2211103 reaction equation
[C:1]1(=[O:11])[O:6][C:4](=[O:5])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[Cl-].[Al+3].[Cl-].[Cl-].[Br:16][C:17]1[S:18][CH:19]=[CH:20][C:21]=1C.Cl>ClC(Cl)C>[Br:16][C:17]1[S:18][C:19]([C:4]([C:3]2[CH:7]=[CH:8][CH:9]=[CH:10][C:2]=2[C:1]([OH:6])=[O:11])=[O:5])=[CH:20][CH:21]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6811Phthalic AnhydrideHCID 843142-Bromo-3-methylthiopheneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 52606402-[(5-bromo-2-thienyl)carbonyl]benzenecarboxylic acid

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

1.90 g of phthalic anhydride and 3.58 g of aluminum chloride were dissolved in 40 ml of dichloroethane, and 2-bromo-3-methylthiophene was added dropwise to the solution at room temperature. After stirring the solution for 4 hours, the reaction solution was poured into a 1-N hydrochloric acid under cooling with ice, and extracted with chloroform. By purifying the extract by silica gel chromatography (eluent: chloroform, ethyl acetate), 1.70 g of o-(5-bromo-2-thenoyl)benzoic acid was obtained.

Workup

  1. temperatureunder cooling with ice
  2. extractionextracted with chloroform
  3. customBy purifying the
  4. extractionextract by silica gel chromatography (eluent: chloroform, ethyl acetate)

Sources & evidence

ORD record
ord-7da177982814474a876f7c3b2239d5ff
Source dataset
uspto-grants-1995_10
Patent number
US05462941

Reaction notes

Loading…