N-bromobutanimide → HCID 118659440, compound

HRID 1477250Notes

Reaction equation

HRID 1477250 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]([CH3:20])([S:16]([CH3:19])(=[O:18])=[O:17])[C:12]([O:14][CH3:15])=[O:13])=[CH:5][CH:4]=1)#[CH:2].C1C(=O)N([Br:28])C(=O)C1>CC(C)=O.[N+]([O-])([O-])=O.[Ag+]>[Br:28][C:2]#[C:1][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:10][C:11]([CH3:20])([S:16]([CH3:19])(=[O:17])=[O:18])[C:12]([O:14][CH3:15])=[O:13])=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 118659596HCID 118659596, compound

Product 1

HCID 118659440HCID 118659440, compoundYield 4.75%

Reagents, catalysts & solvents 2

HCID 24470Silver NitrateCatalystHCID 180AcetoneSolvent

Procedure

To a stirring solution of methyl 4-(4-ethynylphenyl)-2-methyl-2-(methylsulfonyl)butanoate (9.5, 2.49 g, 8.46 mmol) and silver nitrate (144 mg, 0.85 mmol) in acetone (24 mL) was added NBS (2.5 g, 14.33 mmol) and the reaction was stirred at room temperature for 1.5 hr. Solvent was removed under reduced pressure to give a residue, which was purified by flash chromatography (silica gel/30-50% EtOAc/hexanes) to yield methyl 4-(4-(bromoethynyl)phenyl)-2-methyl-2-(methylsulfonyl)butanoate (9.6, 150 mg, 0.40 mmol, 4.75%). MS: m/z calcd for C15H17BrO4S 372.0/374.0. found [M+H]+ 373.0/375.0.

Workup

  1. customSolvent was removed under reduced pressure
  2. customto give a residue, which
  3. customwas purified by flash chromatography (silica gel/30-50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-1899e3da580140fd86c29b43b9f28fec
Source dataset
uspto-grants-2016_08
Patent number
US09403758B2

Reaction notes

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