Sodium Hydroxide → 1-Methanesulfonyl-3-nitro-5-trifluoromethylbenzene

HRID 2200123Notes

Reaction equation

HRID 2200123 reaction equation
Br[C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([N+:12]([O-:14])=[O:13])[CH:3]=1.[CH3:15][S:16]([O-:18])=[O:17].[Na+].[OH-].[Na+]>CS(C)=O>[CH3:15][S:16]([C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([N+:12]([O-:14])=[O:13])[CH:3]=1)(=[O:18])=[O:17]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 2733271Sodium methanesulfinateHCID 70154111-Bromo-3-nitro-5-(trifluoromethyl)benzene

Product 1

HCID 684231001-Methanesulfonyl-3-nitro-5-trifluoromethylbenzeneYield 33.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Stir the mixture of 1-bromo-3-nitro-5-(trifluoromethyl)benzene (6 g, 22.2 mmol), sodium methanesulfinate (2.8 g, 26.7 mmol), cuprous iodide (0.5 g, 2.22 mmol), L(−)-proline (0.5 g, 4.44 mmol) and sodium hydroxide (0.088 g, 4.44 mmol) in DMSO (20 mL) at 100° C. for 15 hrs under nitrogen atmosphere. Add water, extract the mixture with ethyl acetate (200 mL×3), combine the organic layers, dry over anhydrous sodium sulfate, and concentrate the mixture under reduced pressure. Purify the residue by flash chromatography to afford the desired product (2 g, 33.3%).

Workup

  1. extractionAdd water, extract the mixture with ethyl acetate (200 mL×3)
  2. dry with materialdry over anhydrous sodium sulfate
  3. concentrationconcentrate the mixture under reduced pressure
  4. customPurify the residue by flash chromatography

Sources & evidence

ORD record
ord-aa230be9c1b9413dae09329ab2705b47
Source dataset
uspto-grants-2016_06
Patent number
US09359338B2

Reaction notes

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