N-bromobutanimide → HCID 86065640, compound

HRID 1477236Notes

Reaction equation

HRID 1477236 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:11])[CH3:10])=[CH:5][CH:4]=1)#[CH:2].C1C(=O)N([Br:19])C(=O)C1>CC(C)=O.[N+]([O-])([O-])=O.[Ag+]>[Br:19][C:2]#[C:1][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:11])[CH3:10])=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 51236261-(4-Ethynylphenyl)ethan-1-one

Product 1

HCID 86065640HCID 86065640, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 24470Silver NitrateCatalystHCID 180AcetoneSolvent

Procedure

To a stirring solution of compound 1.10 (12 g, 83.3 mmol) in acetone (200 mL) was added AgNO3 (1.34 g, 7.9 mmol) and the the reaction was stirred for 30 min. NBS (17.7 g, 99.96 mmol) was then added and the reaction mixture was stirred at 20° C. for 14 hr. Solids were removed by filtration and the filtrate was concentrated under reduced pressure to give a crude, which was purified by flash chromatography (silica gel/ethyl acetate in petroleum ether 5%-10% v/v) to give compound 1.11 as a white solid (14 g, 76%). 1H NMR (400 MHz, DMSO-d6) δ 7.95 (d, J=8, 2H), 7.62 (d, J=8, 2H), 2.58 (s, 3H).

Workup

  1. stirringthe reaction mixture was stirred at 20° C. for 14 hr
  2. customSolids were removed by filtration
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customto give a crude, which
  5. customwas purified by flash chromatography (silica gel/ethyl acetate in petroleum ether 5%-10% v/v)

Sources & evidence

ORD record
ord-52f61c4f71b3469da6bb5f32261657ec
Source dataset
uspto-grants-2016_08
Patent number
US09403758B2

Reaction notes

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