Azobisisobutyronitrile → [2'-(N-t-Butylsulfamoyl)biphenyl-4-yl]methyl bromide

HRID 257554Notes

Reaction equation

HRID 257554 reaction equation
[Br:1]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N.[C:21]([NH:25][S:26]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[C:35]1[CH:40]=[CH:39][C:38]([CH3:41])=[CH:37][CH:36]=1)(=[O:28])=[O:27])([CH3:24])([CH3:23])[CH3:22]>C(Cl)(Cl)(Cl)Cl>[C:21]([NH:25][S:26]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[C:35]1[CH:40]=[CH:39][C:38]([CH2:41][Br:1])=[CH:37][CH:36]=1)(=[O:28])=[O:27])([CH3:24])([CH3:23])[CH3:22]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 152820992'-(N-t-Butylsulfamoyl)-4-methylbiphenyl

Product 1

HCID 15282100[2'-(N-t-Butylsulfamoyl)biphenyl-4-yl]methyl bromideYield 97%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

N-Bromosuccinimide (387 mg, 2.17 mmol), α,α'-azobis(isobutyronitrile) (catalytic), 2'-(N-t-butylsulfamol)-4-methylbiphenyl (from Step D) (550 mg, 1.81 mmol) and carbon tetrachloride (50 ml) were heated with stirring at reflux for 3 hours. After cooling to room temperature the mixture was filtered and the filtrate evaporated to dryness. Flash chromatography (silica gel, initially 10 and then 20% ethyl acetate-hexane) afforded the title compound [699 mg, 77% pure (the remainder of the material was the corresponding dibromo derivative), 97% yield] as a white solid; 1H NMR (300 MHz, CDCl3) δ8.17 (dd, J=7.5, 1.6 Hz, 1H), 7.68-7.45 (m, 6H), 7.31 (dd, J=7.5, 1.6 Hz, 1H), 4.55 (s, 2H), 3.52 (s, 1H), 1.00 (s, 9H).

Workup

  1. temperatureat reflux for 3 hours
  2. filtrationwas filtered
  3. customthe filtrate evaporated to dryness

Sources & evidence

ORD record
ord-d80c39bc1e4e4307a074df1e86dfc62a
Source dataset
uspto-grants-1993_11
Patent number
US05262412

Reaction notes

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