N-bromobutanimide → HCID 117676170, compound

HRID 1506888Notes

Reaction equation

HRID 1506888 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([F:9])[C:3]=1[CH:10]([CH3:15])[C:11]([O:13][CH3:14])=[O:12].C1C(=O)N([Br:23])C(=O)C1>C(Cl)(Cl)(Cl)Cl.CC(N=NC(C#N)(C)C)(C#N)C>[Br:23][CH2:8][C:6]1[CH:7]=[C:2]([F:1])[C:3]([CH:10]([CH3:15])[C:11]([O:13][CH3:14])=[O:12])=[C:4]([F:9])[CH:5]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 117676155HCID 117676155, compound

Product 1

HCID 117676170HCID 117676170, compoundYield 86.1%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of compound (31b) (2.3 g, 10.7 mmol) in carbon tetrachloride (70 mL) was treated with NBS (2.3 g, 12.9 mmol) in the presence of a catalytic amount of AIBN (0.04 g, 0.02 mmol). The obtained crude product was subjected to silica gel column chromatography and elution with an n-hexane/ethyl acetate (4:1) solution to give 2.7 g (86%) of compound (32b) as clear red oil.

Workup

  1. customThe obtained crude product
  2. washwas subjected to silica gel column chromatography and elution with an n-hexane/ethyl acetate (4:1) solution

Sources & evidence

ORD record
ord-35a5ba11715a4d508097f47658991087
Source dataset
uspto-grants-2015_12
Patent number
US09221786B2

Reaction notes

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