Chlorosuccinimide → HCID 12659717, compound

HRID 1155206Notes

Reaction equation

[Br:1][C:2]([Br:9])([Br:8])[CH2:3][CH2:4][C:5]([Cl:7])=[O:6].[Cl:10]N1C(=O)CCC1=O>S(Cl)(Cl)=O>[Cl:10][CH:4]([CH2:3][C:2]([Br:9])([Br:8])[Br:1])[C:5]([Cl:7])=[O:6]

Participants

Conditions

Temperature: 60 °C

Procedure

343.2 g (1.0 mol) of 4,4,4-tribromobutyric acid chloride are dissolved in 600 g of thionyl chloride, and 266.0 g (2.0 mols) of N-chlorosuccinimide are added in portions at 60° C., whilst at the same time exposing the mixture to a high-pressure mercury lamp. After all of the N-chlorosuccinimide has been added, the resulting mixture is stirred for 5 hours at 60° C., with exposure to the said lamp. The thionyl chloride is then distilled off and the residue is rectified under a high vacuum. 309.7 g (82% of theory) of 2-chloro-4,4,4-tribromobutyric acid chloride with a boiling point of 59° to 63° C./0.05 mm Hg are obtained.

Workup

distillationThe thionyl chloride is then distilled off

Sources & evidence

ORD record: ord-9597fc10eae4425ba6e50faa5562e1a5
Source dataset: uspto-grants-1981_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04299967

Reaction notes

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