2-Fluoro-5-nitrobenzotrifluoride → 1-(Methylsulphonyl)-4-nitro-2-(trifluoromethyl)benzene

HRID 912566Notes

Reaction equation

HRID 912566 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12].[CH3:15][S:16]([O-:18])=[O:17].[Na+]>CN(C=O)C>[CH3:15][S:16]([C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12])(=[O:18])=[O:17]

Participants

4

Reactant 2

HCID 949542-Fluoro-5-nitrobenzotrifluorideHCID 2733271Sodium methanesulfinate

Product 1

HCID 206051531-(Methylsulphonyl)-4-nitro-2-(trifluoromethyl)benzeneYield 64%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 2-fluoro-5-nitro-benzotrifluoride (0.50 g, 2.4 mmol) and sodium methanesulfinate (0.25 g, 2.4 mmol) in anhyd DMF (1.0 mL) was heated at 120° C. with stirring. After 18h the reaction mixture was cooled, concentrated and chromatographed (silica, EtOAc/Hex, 0:100 to 40:60) to give 2-methanesulfonyl-5-nitro-benzotrifluoride (0.41 g, 64%) as a white solid: 1H-NMR (CDCl3) δ 8.76 (1H, d, J=2.0), 8.62 (1H, dd, J=2.0, 8.8), 8.57 (1H, d, J=8.8), 3.26 (3H, s).

Workup

  1. concentrationconcentrated
  2. customchromatographed (silica, EtOAc/Hex, 0:100 to 40:60)

Sources & evidence

ORD record
ord-1d2c7ad9cfc1436ea74bb9568fdc76c4
Source dataset
uspto-grants-2011_09
Patent number
US08026237B2

Reaction notes

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