N-bromobutanimide → HCID 22761172, compound

HRID 1704100Notes

Reaction equation

HRID 1704100 reaction equation
[CH3:1][O:2][C:3](=[O:23])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH2:13][CH2:14][O:15][C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)=[CH:7][CH:6]=1.[Br:24]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:24][CH:4]([C:5]1[CH:6]=[CH:7][C:8]([O:11][CH2:12][CH2:13][CH2:14][O:15][C:16]2[CH:17]=[CH:18][C:19]([Cl:22])=[CH:20][CH:21]=2)=[CH:9][CH:10]=1)[C:3]([O:2][CH3:1])=[O:23]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 22761078HCID 22761078, compound

Product 1

HCID 22761172HCID 22761172, compoundYield 65.7%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 33.5 g of methyl{p-[3-(p-chlorophenoxy)propoxy]phenyl}acetate and 19.6 g of N-bromosuccinimide in 400 ml of carbon tetrachloride is refluxed for 24 hours or until the reaction is complete. The mixture is cooled, filtered and the filtrate passed through a column of silica gel with carbon tetrachloride as eluent to give 27.2 g of product as an oil. Crystallization from petroleum ether gives white crystals, mp 49°-53° C.

Workup

  1. temperatureis refluxed for 24 hours or until the reaction
  2. temperatureThe mixture is cooled
  3. filtrationfiltered

Sources & evidence

ORD record
ord-93a64271962545c2b2fea7315315267c
Source dataset
uspto-grants-1978_11
Patent number
US04125732

Reaction notes

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