Phosphorus pentachloride → 4-Bromo-2-(methoxyimino)-3-oxobutanoyl chloride
Reaction equation
P(Cl)(Cl)(Cl)(Cl)[Cl:2].[Br:7][CH2:8][C:9](=[O:17])[C:10](=[N:14][O:15][CH3:16])[C:11](O)=[O:12]>ClCCl>[Br:7][CH2:8][C:9](=[O:17])[C:10](=[N:14][O:15][CH3:16])[C:11]([Cl:2])=[O:12]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -20 °C
Procedure
To a suspension of phosphorous pentachloride (64.91 gm; 0.3113 moles) in dichloromethane (250 ml), cooled to −20° C. was added a solution of 4-bromo-2-methoxyimino-3-oxo butyric acid (66.41 gm; 0.2965 moles; purity ca. 97%; containing<0.5% of di- and poly-brominated compounds and prepared as per the method disclosed in WO 03/045899) in dichloromethane (250 ml) over a period of 30 minutes at −20° C. to −5° C. The temperature was raised to 5 to 10° C. and the reaction mixture purged with nitrogen gas for one to two hours to expel out hydrogen chloride gas. The solution containing 4-bromo-2-methoxyimino-3-oxo butyric acid chloride (IV) was cooled to −10° C.
Workup
- additioncontaining
- custom<0.5% of di- and poly-brominated compounds and prepared as per the method
- customof 30 minutes
- customat −20° C. to −5° C
- temperatureThe temperature was raised to 5 to 10° C.
- customthe reaction mixture purged with nitrogen gas for one to two hours
- additionThe solution containing 4-bromo-2-methoxyimino-3-oxo butyric acid chloride (IV)
- temperaturewas cooled to −10° C.
Sources & evidence
- ORD record
- ord-c7864346d3c74a85b31f6e28dd9c1373
- Source dataset
- uspto-grants-2008_12
- Patent number
- US07470786B2
Reaction notes
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