N-bromobutanimide → 3-(Bromomethyl)benzene-1-sulfonyl chloride

HRID 2244025Notes

Reaction equation

HRID 2244025 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH3:9][C:10]1[CH:11]=[C:12]([S:16]([Cl:19])(=[O:18])=[O:17])[CH:13]=[CH:14][CH:15]=1>C(Cl)(Cl)(Cl)Cl.CC(N=NC(C#N)(C)C)(C#N)C>[Br:1][CH2:9][C:10]1[CH:11]=[C:12]([S:16]([Cl:19])(=[O:18])=[O:17])[CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 27345953-Methylbenzenesulphonyl chloride

Product 1

HCID 234473893-(Bromomethyl)benzene-1-sulfonyl chlorideYield 37%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

Add N-bromosuccinimide (9.34 g, 52.5 mmol) and AIBN (5 mg, 0.32 mmol) to a solution of 3-methyl-benzenesulfonyl chloride (10.0 g, 52.5 mmol) in carbon tetrachloride (52 mL), and heat the solution at reflux for 12 hours. Filter the mixture to remove solids and condense under reduced pressure to afford a thick oil. Purify by flash chromatography to yield the title compound as an off-white crystalline solid (5.24 g, 19.4 mmol): 1H NMR (CDCl3) δ 4.54 (s, 2H), 7.62 (m, 1H), 7.78 (m, 1H), 7.98 (m, 1H), 8.06 (m, 1H).

Workup

  1. temperatureheat the solution
  2. temperatureat reflux for 12 hours
  3. filtrationFilter the mixture
  4. customto remove
  5. customsolids and condense under reduced pressure
  6. customto afford a thick oil
  7. customPurify by flash chromatography

Sources & evidence

ORD record
ord-aef9790ddf794e36b75a7741f6445f7c
Source dataset
uspto-grants-2010_03
Patent number
US07678794B2

Reaction notes

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