N-bromobutanimide → HCID 54271297, compound

HRID 1704084Notes

Reaction equation

HRID 1704084 reaction equation
[CH3:1][O:2][C:3](=[O:21])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][O:13][C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)=[CH:7][CH:6]=1.[Br:22]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:22][CH:4]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][O:13][C:14]2[CH:15]=[CH:16][C:17]([Cl:20])=[CH:18][CH:19]=2)=[CH:7][CH:6]=1)[C:3]([O:2][CH3:1])=[O:21]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 22761139HCID 22761139, compound

Product 1

HCID 54271297HCID 54271297, compoundYield 87.1%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 23.3 g of methyl{p-[(p-chlorophenoxy)methoxy]phenyl}acetate in 300 ml of carbon tetrachloride is added 14.2 g of N-bromosuccinimide. The mixture is stirred and refluxed for 24 hours or until reaction is complete. The mixture is cooled, filtered and the filtrate poured through a column of silica gel (60-200 mesh). Cuts (250 ml) are taken with carbon tetrachloride eluent. The product is collected in fractions 2-6 to give 25.5 g of product as an oil.

Workup

  1. temperaturerefluxed for 24 hours or until reaction
  2. temperatureThe mixture is cooled
  3. filtrationfiltered
  4. additionthe filtrate poured through a column of silica gel (60-200 mesh)
  5. customThe product is collected in fractions 2-6

Sources & evidence

ORD record
ord-e8d99e450bb749588d68bd90a2376cb8
Source dataset
uspto-grants-1978_11
Patent number
US04125732

Reaction notes

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