N-bromobutanimide → 1-Bromo-2-p-tolylsulfonylacetylene

HRID 1660715Notes

Reaction equation

HRID 1660715 reaction equation
C[Si]([C:5]#[C:6][S:7]([C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=1)(=[O:9])=[O:8])(C)C.[Br:17]N1C(=O)CCC1=O>CC(C)=O.[N+]([O-])([O-])=O.[Ag+]>[Br:17][C:5]#[C:6][S:7]([C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=1)(=[O:9])=[O:8]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 5075769p-Tolyl [2-(trimethylsilyl)ethynyl] sulfone

Product 1

HCID 106589111-Bromo-2-p-tolylsulfonylacetyleneYield 96.5%

Reagents, catalysts & solvents 2

HCID 24470Silver NitrateCatalystHCID 180AcetoneSolvent

Procedure

To a stirred solution of trimethylsilyl p-tolylsulfonylacetylene (10 g, 40 mmol) in acetone (300 mL) was added silver nitrate (0.68 g, 4 mmol) followed by the addition of N-bromosuccinimide (7.6 g, 44 mmol) in one portion. The mixture was stirred at room temperature for 1 h. The resulting precipitate was filtered and washed with acetone. Silica gel (20 g) was added to the filtrate and the solvent was removed under reduced pressure. The residue was subjected to column chromatography with hexane/EtOAc (5:1) to afford the product as a light yellow solid (10 g, 96%). Mp. 99-101° C. 1H NMR (CDCl3) δ 7.87 (d, 2H, J=7.8 Hz), 7.39 (d, 2H, J=7.8 Hz), 2.47 (s, 3H); 13C NMR (CDCl3) δ 146.19, 138.16, 130.34, 127.83, 78.14, 61.70, 21.97.

Workup

  1. filtrationThe resulting precipitate was filtered
  2. washwashed with acetone
  3. additionSilica gel (20 g) was added to the filtrate
  4. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-22a904764ac649dc935e1dafed2d5676
Source dataset
uspto-grants-2011_10
Patent number
US08030300B2

Reaction notes

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