4-Iodo-1-benzothiophene-2-carboxylic acid → HCID 21838135, compound

HRID 1740296Notes

Reaction equation

HRID 1740296 reaction equation
C([C:4]1[S:8][C:7]2[CH:9]=[CH:10][CH:11]=[C:12]([I:13])[C:6]=2[CH:5]=1)(O)=O>N1C2C(=CC=CC=2)C=CC=1.C(OCC)(=O)C.CCOCC.[Cu]>[I:13][C:12]1[C:6]2[CH:5]=[CH:4][S:8][C:7]=2[CH:9]=[CH:10][CH:11]=1

Participants

6

Reactant 1

HCID 218383524-Iodo-1-benzothiophene-2-carboxylic acid

Product 1

HCID 21838135HCID 21838135, compoundYield 90.6%

Reagents, catalysts & solvents 4

HCID 23978CopperCatalystHCID 3283Diethyl EtherSolventHCID 7047QuinolineSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
200 °C

Procedure

A mixture of 2-carboxy-4-iodobenzo[b]thiophene (2 g) and copper powder (0.05 g) in quinoline (10 ml) was heated at 200° C. for 2 hours. The reaction mixture was cooled to room temperature and diluted with ethyl acetate (50 ml) and ether (50 ml). The mixture was washed with 5% hydrochloric acid solution (3 times) and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel eluting with toluene to afford 4-iodobenzo[b]thiophene (1.55 g).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washThe mixture was washed with 5% hydrochloric acid solution (3 times) and brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was purified by column chromatography on silica gel eluting with toluene

Sources & evidence

ORD record
ord-3b52d76947aa4170992869cab9daaa83
Source dataset
uspto-grants-1999_10
Patent number
US05968985

Reaction notes

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