Carbon Dioxide → Benzo(b)thiophene-3-carboxylic acid
Reaction equation
[CH:1]1[CH:6]=[C:5]2[C:7](Br)=[CH:8][S:9][C:4]2=[CH:3][CH:2]=1.[Li]CCCC.[C:16](=[O:18])=[O:17]>CCOCC>[S:9]1[CH:8]=[C:7]([C:16]([OH:18])=[O:17])[C:5]2[CH:6]=[CH:1][CH:2]=[CH:3][C:4]1=2Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
3-bromothianaphthene (1.63 g, 7.65 mmol) was dissolved in anhydrous ether (30 ml) and n-BuLi (2.5 M, 3.5 ml, 8.65 mmol) was added to the solution at −78° C. The mixture was stirred at −78° C. for 10 min, and then the reaction solution was slowly added to an excessive amount of dry ice dissolved in anhydrous ether (140) under nitrogen conditions. The mixture was heated to room temperature for 1 hour, and then stirred at room temperature for another 2 hours. After the reaction was completed, the product was washed, filtered, and dried to obtain benzo[b]thiophene-3-carboxylic acid (805 mg, 4.51 mmol).
Workup
- temperatureThe mixture was heated to room temperature for 1 hour
- stirringstirred at room temperature for another 2 hours
- washthe product was washed
- filtrationfiltered
- customdried
Sources & evidence
- ORD record
- ord-6beed28d3ba24285989d675db67f3d8a
- Source dataset
- uspto-grants-2012_12
- Patent number
- US08324246B2
Reaction notes
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