Dimethylformamide → 3-Chloro-5-methylthiophene-2-carbonyl chloride
Reaction equation
[C:1]([C:4]1[S:5][C:6]([CH3:10])=[CH:7][C:8]=1[Cl:9])(O)=[O:2].C(Cl)(=O)C([Cl:14])=O.CN(C=O)C>C(Cl)Cl>[Cl:14][C:1]([C:4]1[S:5][C:6]([CH3:10])=[CH:7][C:8]=1[Cl:9])=[O:2]Participants
5
Procedure
To a suspension of 2-carboxy-3-chloro-5-methylthiophene (1.2 g, 6.6 mmol) in methylene chloride (16 mL) at 0° C. were added oxalyl chloride (0.6 mL, 7.3 mmol) and a drop of DMF. The mixture was stirred at ambient temperature for 5 hours, then concentrated of all volatiles and dried in vacuo to afford 1.3 g (quantitative yield) of 2-chlorocarbonyl-3-chloro-5-methylthiophene as a pale yellow solid; NMR (DMSO-d6 /TFA) 7.4 (s, 1), 2.5 (s, 3) ppm.
Workup
- concentrationconcentrated of all volatiles
- customdried in vacuo
Sources & evidence
- ORD record
- ord-1e1863ebb6b748a9965212deca45180b
- Source dataset
- uspto-grants-2000_10
- Patent number
- US06140351
Reaction notes
Loading…