HuagongsheHuagongshe Chemistry Print Report · For research reference only
Thionyl Chloride → Methyl 2-bromo-4-chloro4-oxobutanoate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Thionyl Chloride | HCID 24386 | — |
| Reactant | 3-Bromo-4-methoxy-4-oxobutanoic acid | HCID 11789071 | — |
| Catalyst | Dimethylformamide | HCID 6228 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | Methyl 2-bromo-4-chloro4-oxobutanoate | HCID 11390578 | 100% |
Reaction Steps
Thionyl chloride (6.54 g, 54.9 mmol) in dichloromethane (7 mL) was added dropwise over 30 minutes to a mixture of 1-methyl hydrogen bromobutanedioate (i.e. the product of Step A) (10 g, 47.4 mmol) and N,N-dimethylformamide (5 drops) in dichloromethane (20 mL) heated at reflux. The mixture was heated at reflux for an additional 60 minutes and then allowed to cool to room temperature. The solvent was removed under reduced pressure to leave the title product as an oil (11 g, about 100% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07834186B2 |
| Source dataset | uspto-grants-2010_11 |
| ORD ID | ord-34087a3c05b948d4953d1e21ca11448a |
| Source note | uspto-grants-2010_11 |