Toluene → HCID 4640240, compound

HRID 1018959Notes

Reaction equation

HRID 1018959 reaction equation
Br[CH:2]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:3]([O-:5])=[O:4].[NH:12]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[N:14]=[N:13]1.[C:21]1(C)C=CC=CC=1>C(Cl)(Cl)Cl>[N:12]1([CH:2]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:3]([O:5][CH3:21])=[O:4])[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[N:14]=[N:13]1

Participants

5

Reactant 3

HCID 1140TolueneHCID 22017357Bromo(phenyl)acetateHCID 178418385HCID 178418385, compound

Product 1

HCID 4640240HCID 4640240, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of methyl ?-bromophenylacetate (6.9 g) and benzotriazole (11 g) in 50 mL of toluene was heated to reflux for 22 h, cooled and diluted with 400 mL of CHCl3. The mixture was then washed with 100 mL of 10% aqueous NaOH and the organic layer was dried over Na2SO4 and concentrated. After swishing from 1:1 hexane/EtOAc, 5.7 g of the title compound was obtained as a white solid.

Workup

  1. additionA mixture of methyl
  2. temperatureto reflux for 22 h
  3. temperaturecooled
  4. washThe mixture was then washed with 100 mL of 10% aqueous NaOH
  5. dry with materialthe organic layer was dried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f6119e89ff5748f09e069a3067e7112b
Source dataset
uspto-grants-2002_11
Patent number
US06486141B2

Reaction notes

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