N-bromobutanimide → methyl (2Z)-2-bromo-2-[(2-chlorophenyl)hydrazinylidene]acetate

HRID 7405Notes

Reaction equation

HRID 7405 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8]/[N:9]=[CH:10]/[C:11]([O:13][CH3:14])=[O:12].[Br:15]N1C(=O)CCC1=O>O1CCCC1>[Br:15]/[C:10](=[N:9]\[NH:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[Cl:1])/[C:11]([O:13][CH3:14])=[O:12]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 19868318methyl (2E)-2-[(2-chlorophenyl)hydrazinylidene]acetate

Product 1

HCID 140475537methyl (2Z)-2-bromo-2-[(2-chlorophenyl)hydrazinylidene]acetateYield 71.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the title compound of Step A (16.5 g, 77 mmol) in tetrahydrofuran (150 mL) was added N-bromosuccinimide (13.7 g, 77 mmol) and the mixture was stirred at ambient temperature for 2 hours. The mixture was concentrated and extracted with hexane and the hexane solution was concentrated to give the title compound of Step B (16 g) as an orange solid.

Workup

  1. concentrationThe mixture was concentrated
  2. extractionextracted with hexane
  3. concentrationthe hexane solution was concentrated

Sources & evidence

ORD record
ord-a30fcfbaca0f4f4f879d97038b13ac03
Source dataset
uspto-grants-2006_08
Patent number
US07087598B2

Reaction notes

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