Quinoline → 6-Bromo-benzo[b]thiophene
Reaction equation
N1C2C(=CC=CC=2)C=CC=1.[Br:11][C:12]1[CH:23]=[CH:22][C:15]2[CH:16]=[C:17](C(O)=O)[S:18][C:14]=2[CH:13]=1>[Cu].CCOCC>[Br:11][C:12]1[CH:23]=[CH:22][C:15]2[CH:16]=[CH:17][S:18][C:14]=2[CH:13]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 220 °C
Procedure
To quinoline (45 ml) were added 6-bromobenzothiophene -2-carboxylic acid (14 g) and copper powder (874 mg), followed by stirring under heat at an oil temperature of 220° C. for 2 hours. After the reaction mixture was allowed to cool down, ether was added and the copper powder was filtered off. The filtrate was washed with a 1N aqueous solution of hydrochloric acid, then with a 1N aqueous solution of sodium hydroxide and finally with saturated aqueous NaCl solution, followed by drying over anhydrous sodium sulfate. The solvent was then distilled off under reduced pressure. The residue was purified by chromatography on a silica gel column (hexane), whereby the title compound (5.56 g) was obtained as a pale yellow solid. In addition, the raw material (3.15 g) was recovered.
Workup
- temperatureto cool down
- filtrationthe copper powder was filtered off
- washThe filtrate was washed with a 1N aqueous solution of hydrochloric acid
- dry with materialby drying over anhydrous sodium sulfate
- distillationThe solvent was then distilled off under reduced pressure
- customThe residue was purified by chromatography on a silica gel column (hexane), whereby the title compound (5.56 g)
- customwas obtained as a pale yellow solid
- customIn addition, the raw material (3.15 g) was recovered
Sources & evidence
- ORD record
- ord-b83f0edea64c4b2bb9994d17a4c7920b
- Source dataset
- uspto-grants-2004_06
- Patent number
- US06747023B1
Reaction notes
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