N-bromobutanimide → HCID 10881860, compound

HRID 42336Notes

Reaction equation

HRID 42336 reaction equation
[C:1]([NH:5][S:6]([C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][C:10]=1[F:16])(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C(=O)N([Br:24])C(=O)C1>C(Cl)(Cl)(Cl)Cl.CC(N=NC(C#N)(C)C)(C#N)C>[Br:24][CH2:15][C:12]1[CH:13]=[CH:14][C:9]([S:6]([NH:5][C:1]([CH3:4])([CH3:3])[CH3:2])(=[O:7])=[O:8])=[C:10]([F:16])[CH:11]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 11107608N-tert-butyl-2-fluoro-4-methylbenzenesulfonamide

Product 1

HCID 10881860HCID 10881860, compoundYield 79.5%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of N-tert-butyl-2-fluoro-4-methylbenzenesulfonamide (2 g), NBS (1.16 g) and AIBN (40 mg) in CCl4 (25 ml) was refluxed for 3 hours. The reaction mixture was cooled, filtered and concentrated to give a viscous syrup, which was purified by silica gel column chromatography to give 1.68 g 4-(bromomethyl)-N-tert-butyl-2-fluorobenzenesulfonamide as a colorless crystal solid.

Workup

  1. temperaturewas refluxed for 3 hours
  2. temperatureThe reaction mixture was cooled
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give a viscous syrup, which
  6. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-de8c6aea1b5b471bb9a7eb52a9c13dc2
Source dataset
uspto-grants-2013_09
Patent number
US08536187B2

Reaction notes

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