Bromine → 4'-(Bromomethyl)-N-t-butyl-3'-fluoro-2-biphenylsulfonamide

HRID 1648345Notes

Reaction equation

HRID 1648345 reaction equation
[C:1]([NH:5][S:6]([C:9]1[C:10]([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[C:17]([F:22])[CH:16]=2)=[CH:11][CH:12]=[CH:13][CH:14]=1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Br:23]Br>C(Cl)(Cl)(Cl)Cl.[W]>[Br:23][CH2:21][C:18]1[CH:19]=[CH:20][C:15]([C:10]2[C:9]([S:6]([NH:5][C:1]([CH3:4])([CH3:3])[CH3:2])(=[O:8])=[O:7])=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:16][C:17]=1[F:22]

Participants

5

Reactant 2

HCID 24408BromineHCID 100874243-Fluoro-4-methyl-2'-(N-t-butylsulfamoyl)biphenyl

Product 1

HCID 100465214'-(Bromomethyl)-N-t-butyl-3'-fluoro-2-biphenylsulfonamideYield 81.8%

Reagents, catalysts & solvents 2

HCID 23964TungstenCatalystHCID 5943Carbon TetrachlorideSolvent2×

Procedure

A solution of 1.08 g (3.36 mmol) of N-t-butyl-3'-fiuoro-4'-methyl-2-biphenylsulfonamide (from Step E) in 20 in mL of CCl4 was stirred at reflux under irradiation from a 100-watt tungsten lamp as a solution of 3.5 mmol of bromine in approximately 13 mL of CCl4 was added dropwise over 1.5 hour. After being stirred at reflux overnight, the solution was cooled and concentrated. The residue was crystallized from EtOAc-hexane to give 1.10 g of the title compound as an off-white solid, mp 138°-140° C. (estimated purity 87%, containing minor unbrominated and dibrominated contaminants by TLC); mass spectrum (FAB) m/e 400, 402 (M+1)+.

Workup

  1. additionwas added dropwise over 1.5 hour
  2. temperatureat reflux overnight
  3. temperaturethe solution was cooled
  4. concentrationconcentrated
  5. customThe residue was crystallized from EtOAc-hexane
  6. customto give

Sources & evidence

ORD record
ord-ace736ab4f7849b9836cf27b92881f51
Source dataset
uspto-grants-1995_07
Patent number
US05436259

Reaction notes

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