Sodium Hydroxide → 1-Bromo-3-(methanesulfonyl)-5-methylbenzene

HRID 1046657Notes

Reaction equation

HRID 1046657 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH3:9])[CH:5]=[C:6](Br)[CH:7]=1.[CH3:10][S:11]([O-:13])=[O:12].[Na+].N1CCC[C@H]1C(O)=O.[OH-].[Na+]>O.[Cu]I>[Br:1][C:2]1[CH:3]=[C:4]([CH3:9])[CH:5]=[C:6]([S:11]([CH3:10])(=[O:13])=[O:12])[CH:7]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 153613,5-DibromotolueneHCID 145742L-ProlineHCID 2733271Sodium methanesulfinate

Product 1

HCID 592512981-Bromo-3-(methanesulfonyl)-5-methylbenzeneYield 60.2%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolvent

Conditions

Temperature
210 °C

Procedure

A mixture of 3,5-dibromotoluene (2.0 g, 8.0 mmol), sodium methanesulfinate (0.92 g, 9.0 mmol), copper(I) iodide (152 mg, 0.8 mmol), proline (0.18 g, 1.6 mmol) and sodium hydroxide (64 mg, 1.6 mmol) in DSMO (15 mL, anhyd) was heated in a microwave unit (Biotage Initiator™) at 210° C. for min. The reaction was repeated two more times and the reaction mixtures were combined, diluted with H2O and extracted with EtOAc. The combined extracts were washed with H2O and brine, then dried (Na2SO4), concentrated and purified by chromatography (silica, EtOAc/Hex, 0:100 to 40:60) to give the title compound (1.2 g, 20% combined yield) as a white solid. GC-MS (EI): 248, 250.

Workup

  1. customthe reaction mixtures
  2. extractionextracted with EtOAc
  3. washThe combined extracts were washed with H2O and brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. custompurified by chromatography (silica, EtOAc/Hex, 0:100 to 40:60)

Sources & evidence

ORD record
ord-49b080aaef34439895cd5e9145f0a8ff
Source dataset
uspto-grants-2013_10
Patent number
US08569352B2

Reaction notes

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