Azobisisobutyronitrile → HCID 20526231, compound
Reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][CH2:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])=[CH:4][CH:3]=1.[Br:17]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.N(C(C)(C)C#N)=NC(C)(C)C#N>>[Br:17][CH:7]([O:6][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:16][CH:15]=1)[C:8]([O:10][C:11]([CH3:13])([CH3:12])[CH3:14])=[O:9]Participants
5
Procedure
German Laid-Open Application DOS 2,720,654 discloses that alkanecarboxylic acid derivatives, for example tert.-butyl 4-chlorophenoxyacetate, can be reacted with N-bromosuccinimide in the presence of a solvent and of a source of free radicals, such as dibenzoyl peroxide or azo-bis-isobutyronitrile, to give tert.-butyl bromo-(4-chlorophenoxy)-acetate. In the case of tert.-butyl 4-chlorophenoxyacetate it is stated that a reaction time of 2 hours is required and a yield of 76 percent is obtained. If the process is carried out with the corresponding propionic acid esters, especially on an industrial scale, substantially longer reaction times, for example from 8 to 15 hours, are required to obtain yields of from 60 to 80% of theory.
Sources & evidence
- ORD record
- ord-135fc921fc9a480c9aa085d64c35458b
- Source dataset
- uspto-grants-1982_09
- Patent number
- US04348534
Reaction notes
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