Thionyl Chloride → HCID 12659717, compound

HRID 1733428Notes

Reaction equation

HRID 1733428 reaction equation
[Br:1][C:2]([Br:9])([Br:8])[CH2:3][CH2:4][C:5]([Cl:7])=[O:6].S(Cl)([Cl:12])=O.ClN1C(=O)CCC1=O>>[Cl:12][CH:4]([CH2:3][C:2]([Br:9])([Br:8])[Br:1])[C:5]([Cl:7])=[O:6]

Participants

4

Reactant 3

HCID 24386Thionyl ChlorideHCID 31398Chlorosuccinimide2×HCID 13100663HCID 13100663, compound

Product 1

HCID 12659717HCID 12659717, compoundYield 82%

Conditions

Temperature
60 °C

Procedure

To a solution of 343,2 g (1 mole) 4,4,4-tribromobutyric acid chloride in 600 g of thionylchloride 266,0 g (2 mole) of N-chlorosuccinimide is added portion wise at 60° C. while the reaction mixture is irradiated with a mercury high-pressure lamp. After addition of the N-chlorosuccinimide the reaction mixture is stirred for 5 hours at 60° C. while irradiation is continued. Then the thionyl chloride is evaporated and the residue is distilled in vacuo. 309.7 (82% of theory) of 2-chloro-4,4,4-tribromobutyric acid chloride, b.p. 59°-63° C./0,05 torr is obtained.

Workup

  1. customis irradiated with a mercury high-pressure lamp
  2. customThen the thionyl chloride is evaporated
  3. distillationthe residue is distilled in vacuo

Sources & evidence

ORD record
ord-76a99b2e981e4a3da33928c06f217657
Source dataset
uspto-grants-1980_12
Patent number
US04242278

Reaction notes

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