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

HRID 221082Notes

Reaction equation

HRID 221082 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. (3) The above 6-chlorobenzo[b]thiophene and 5-bromo-2-chlorobenzaldehyde obtained in Reference Example 16-(1) were treated in a manner similar to Reference Example 7 to give 5-bromo-2-chloro-1-(6-chlorobenzo[b]thiophen-2-ylmethyl)benzene 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-1e6f21d8bdf547a6bed7715877d98e71
Source dataset
uspto-grants-2012_06
Patent number
US08202984B2

Reaction notes

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