Thionyl Chloride → 4-Bromo-3-methylthiophene-2-carbonyl chloride
Reaction equation
[Br:1][C:2]1[C:3]([CH3:10])=[C:4]([C:7](O)=[O:8])[S:5][CH:6]=1.S(Cl)([Cl:13])=O>CN(C=O)C.ClCCCl>[Br:1][C:2]1[C:3]([CH3:10])=[C:4]([C:7]([Cl:13])=[O:8])[S:5][CH:6]=1Participants
5
Procedure
A slurry of 1.11 g (5 mmole) of 4-bromo-3-methyl-2-thiophenecarboxylic acid, 0.44 mL (6 mmole) of thionyl chloride, 5 drops of DMF, and 10 mL of 1,2-dichloroethane was heated at 80° C. for 1.5 h. The clear solution was cooled and concentrated on a roto-evaporator. The residue was dissolved in 5 mL of 1,2-dichloroethane and reconcentrated on a roto-evaporator to give 1.2 g of a tan solid, 97% pure (GC area). This acid chloride was used without further purification.
Workup
- temperatureThe clear solution was cooled
- concentrationconcentrated on a roto-evaporator
- dissolutionThe residue was dissolved in 5 mL of 1,2-dichloroethane
- customreconcentrated on a roto-evaporator
Sources & evidence
- ORD record
- ord-dd58aa7ca3fa4d66aeee2cca4d152b3d
- Source dataset
- uspto-grants-2001_12
- Patent number
- US06329528B1
Reaction notes
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