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

HRID 1514548Notes

Reaction equation

HRID 1514548 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-85e04b8dbc3d481aaf3b4e230b04b71f
Source dataset
uspto-grants-2012_07
Patent number
US08222219B2

Reaction notes

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