6-Chloro-1-benzothiophene-2-carboxylic acid → 6-Chloro-1-benzothiophene

HRID 1625810Notes

Reaction equation

HRID 1625810 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:9]=[C:8](C(O)=O)[S:7][C:6]=2[CH:13]=1>N1C2C(=CC=CC=2)C=CC=1.C(OCC)C.[Cu]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:9]=[CH:8][S:7][C:6]=2[CH:13]=1

Participants

5

Reactant 1

HCID 71419196-Chloro-1-benzothiophene-2-carboxylic acid

Product 1

HCID 123986016-Chloro-1-benzothiopheneYield 75.2%

Reagents, catalysts & solvents 3

HCID 23978CopperCatalystHCID 3283Diethyl EtherSolventHCID 7047QuinolineSolvent

Procedure

A solution of the above 6-chlorobenzo[b]thiophen-2-ylcarboxylic acid (3.0 g) and copper powder (1.2 g) in quinoline (20 ml) was stirred at 210° C. for 40 minutes. The mixture was cooled to room temperature and diluted with diethyl ether, and insoluble materials were filtered off. The filtrate was washed successively with 10% aqueous hydrochloric acid solution and brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane) to give 6-chlorobenzo[b]thiophene (1.79 g) as colorless crystals.

Workup

  1. filtrationwere filtered off
  2. washThe filtrate was washed successively with 10% aqueous hydrochloric acid solution and brine
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (hexane)

Sources & evidence

ORD record
ord-acba3726e38c4cf994dd0a81839ed381
Source dataset
uspto-grants-2014_07
Patent number
US08785403B2

Reaction notes

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