N-bromobutanimide → HCID 22282466, compound

HRID 1062660Notes

Reaction equation

HRID 1062660 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:9](=[O:15])[CH2:10][C:11]([O:13][CH3:14])=[O:12])[CH:6]=[CH:7][CH:8]=1)#[N:2].[Br:16]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:16][CH:10]([C:9]([C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([C:1]#[N:2])[CH:4]=1)=[O:15])[C:11]([O:13][CH3:14])=[O:12]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 22282423HCID 22282423, compound

Product 1

HCID 22282466HCID 22282466, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of methyl 3-(3-cyanophenyl)-3-oxopropionate (0.91 g, 4.48 mmol) in 20 mL of carbon tetrachloride at 0° C. was added N-bromosuccinimide (0.80 g, 4.48 mmol). The resulting solution was allowed warm to 25° C. and was stirred for 2 h. The insoluble succinimide was filtered off and the solution was concentrated in vacuo to afford an oil (1.2 g, 95%) which was sufficiently pure to be used without purification. MS(H2O GC-MS) 282/284 (M+H)+.

Workup

  1. filtrationThe insoluble succinimide was filtered off
  2. concentrationthe solution was concentrated in vacuo

Sources & evidence

ORD record
ord-151cfe8f2acb41baac29172d0e8349d4
Source dataset
uspto-grants-2005_11
Patent number
US06962935B2

Reaction notes

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