Phosphorus pentachloride → 4-Bromo-2-(methoxyimino)-3-oxobutanoyl chloride

HRID 231341Notes

Reaction equation

HRID 231341 reaction equation
[Br:1][CH2:2][C:3](=[O:11])[C:4](=[N:8][O:9][CH3:10])[C:5](O)=[O:6].P(Cl)(Cl)(Cl)(Cl)[Cl:13]>C(Cl)Cl>[Br:1][CH2:2][C:3](=[O:11])[C:4](=[N:8][O:9][CH3:10])[C:5]([Cl:13])=[O:6]

Participants

4

Procedure

In 15 ml of methylene chloride was dissolved 2.02 g of 4-bromo-2-methoxyimino-3-oxobutyric acid, followed by addition of 2.06 g of phosphorus pentachloride in small portions at 0°-5° C. The mixture was stirred at the same temperature for 5 minutes and, then, at 20°-25° C. for 1 hour, after which it was concentrated under reduced pressure. To the residue was added 20 ml of hexane and the mixture was stirred for a while and allowed to stand. The supernatant was concentrated under reduced pressure to give 2.1 g of 4-bromo-2-methoxyimino-3-oxobutyryl chloride as oil. Yield 96%.

Workup

  1. waitat 20°-25° C. for 1 hour
  2. concentrationafter which it was concentrated under reduced pressure
  3. additionTo the residue was added 20 ml of hexane
  4. stirringthe mixture was stirred for a while
  5. concentrationThe supernatant was concentrated under reduced pressure

Sources & evidence

ORD record
ord-095d3c28a2a5449a9953d615a668ffbb
Source dataset
uspto-grants-1989_07
Patent number
US04845257

Reaction notes

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