Methanesulfinic acid → 4-Bromo-1-(methanesulfonyl)-2-methylbenzene

HRID 1676200Notes

Reaction equation

HRID 1676200 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](I)=[C:4]([CH3:9])[CH:3]=1.[CH3:10][S:11]([OH:13])=[O:12].[Na]>[Cu]I.CS(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:11]([CH3:10])(=[O:13])=[O:12])=[C:4]([CH3:9])[CH:3]=1

Participants

6

Reactant 3

HCID 87251Methanesulfinic acidHCID 27246015-Bromo-2-iodotolueneHCID 5360545Sodium

Product 1

HCID 206167654-Bromo-1-(methanesulfonyl)-2-methylbenzene

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
125 °C

Procedure

A mixture of 4-bromo-1-iodo-2-methylbenzene (240 μL, 1.68 mmol, Aldrich), Copper(I) iodide (353 mg, 1.85 mmol, Alfa Aesar), Methanesulfinic acid, sodium salt (688 mg, 6.74 mmol, Alfa Aesar) and DMSO (7.2 mL) was purged with Argon and then heated under microwave condition at 125° C. for 20 min. The resulting mixture was stirred at 100° C. for 3 h and then cooled to room temperature. The reaction mixture was diluted with H2O and extracted with EtOAc (2×). The organic layers were combined and washed with brine, dried over Na2SO4 and concentrated in vacuo to a white solid. The solid was purified by flash chromatography (SiO2, 0-50% EtOAc in hexanes) to yield 270 mg of desired product as a white solid. MS (ESI) 249 (M+H).

Workup

  1. customwas purged with Argon
  2. temperaturecooled to room temperature
  3. additionThe reaction mixture was diluted with H2O
  4. extractionextracted with EtOAc (2×)
  5. washwashed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo to a white solid
  8. customThe solid was purified by flash chromatography (SiO2, 0-50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-9216477e97a04b4cb160f648e08df23c
Source dataset
uspto-grants-2011_08
Patent number
US08003796B2

Reaction notes

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