N-bromobutanimide → HCID 60155618, compound

HRID 1506887Notes

Reaction equation

HRID 1506887 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([F:9])=[CH:4][C:3]=1[CH:10]([CH3:15])[C:11]([O:13][CH3:14])=[O:12].[Br:16]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:16][CH2:8][C:6]1[C:5]([F:9])=[CH:4][C:3]([CH:10]([CH3:15])[C:11]([O:13][CH3:14])=[O:12])=[C:2]([F:1])[CH:7]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 60155617HCID 60155617, compound

Product 1

HCID 60155618HCID 60155618, compoundYield 106.3%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of compound (31a) (3.3 g, 15.4 mmol) in carbon tetrachloride (100 mL) was treated with N-bromosuccinimide (NBS) (3.3 g, 18.5 mmol) in the presence of a catalytic amount of azo(bis)isobutyronitrile (AIBN) (0.05 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 4.8 g (90%) of compound (32a) 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-698aba8217aa45a3959accb2f24b1842
Source dataset
uspto-grants-2015_12
Patent number
US09221786B2

Reaction notes

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