p-Tolyl methyl sulfone → 2-Bromo-4-(methanesulfonyl)-1-methylbenzene

HRID 1406309Notes

Reaction equation

HRID 1406309 reaction equation
[Br:1]Br.[CH3:3][S:4]([C:7]1[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][CH:8]=1)(=[O:6])=[O:5]>[Fe]>[Br:1][C:11]1[CH:12]=[C:7]([S:4]([CH3:3])(=[O:5])=[O:6])[CH:8]=[CH:9][C:10]=1[CH3:13]

Participants

4

Reactant 2

HCID 18521p-Tolyl methyl sulfoneHCID 24408Bromine

Product 1

HCID 532169872-Bromo-4-(methanesulfonyl)-1-methylbenzeneYield 80%

Reagents, catalysts & solvents 1

HCID 23925IronCatalyst

Procedure

To a solution of elemental iron (67 mg, 1.2 mmol) in Br2 (2.05 mL, 39.9 mmol) was added 4-methanesulfonyl-1-methyl-benzene (340 mg, 2.0 mmol) at 0° C. The reaction mixture was stirred at room temperature for 2 hrs. TLC (petroleum ether:EtOAc 3:1) indicated the reaction was completed. Then the mixture was poured into an ice-cold aqueous Na2S2SO3 (1M, 10 mL) and extracted with EtOAc (20 mL×3), washed with brine (10 mL×3), dried over sodium sulfate, concentrated in vacuum, and the residue was purified by a Biotage silica gel cartridge (petroleum ether/EtOAc 3:1, Rf˜0.6) to give the title compound (300 mg, 80%) as a white solid.

Workup

  1. extractionextracted with EtOAc (20 mL×3)
  2. washwashed with brine (10 mL×3)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuum
  5. customthe residue was purified by a Biotage silica gel cartridge (petroleum ether/EtOAc 3:1, Rf˜0.6)

Sources & evidence

ORD record
ord-09516a5430b442beb5b61e85dc6e70f1
Source dataset
uspto-grants-2014_12
Patent number
US08916593B2

Reaction notes

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