7-Chloro-1-benzothiophene-2-carboxylic acid → 7-Chloro-1-benzothiophene
Reaction equation
[Cl:1][C:2]1[C:7]2[S:8][C:9](C(O)=O)=[CH:10][C:6]=2[CH:5]=[CH:4][CH:3]=1>N1C2C(=CC=CC=2)C=CC=1.Cl.[Cu]>[Cl:1][C:2]1[C:7]2[S:8][CH:9]=[CH:10][C:6]=2[CH:5]=[CH:4][CH:3]=1Participants
5
Reactant 1
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 190 °C
Procedure
7-Chlorobenzo[b]thiophene-2-carboxylic acid (2.5 g, 11.8 mmol) was suspended in quinoline (20 mL) and treated with copper (0.779 g, 13 mmol). The mixture was heated to 190° C. After 1.5 h, the mixture was allowed to cool down to room temperature and diluted with 200 mL of 2 N HCl. The mixture was extracted three times with ethyl acetate. All the organic layers were combined and washed with 1 N HCl, water and brine, then dried with sodium sulfate. Purification was achieved by flash chromatography using 10 to 20% ethyl acetate in hexanes. Yield=1.8 g.
Workup
- temperatureto cool down to room temperature
- extractionThe mixture was extracted three times with ethyl acetate
- washwashed with 1 N HCl, water and brine
- dry with materialdried with sodium sulfate
- customPurification
Sources & evidence
- ORD record
- ord-8749595312584b2b836dcab0d97aa00f
- Source dataset
- uspto-grants-2010_12
- Patent number
- US07858785B2
Reaction notes
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