Sodium methanesulfinate → 2-Fluoro-1-(2-(methylsulfonyl)ethyl)-4-nitrobenzene

HRID 1843029Notes

Reaction equation

HRID 1843029 reaction equation
Br[CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:5]=1[F:13].[CH3:14][S:15]([O-:17])=[O:16].[Na+]>C(O)(C)C>[F:13][C:5]1[CH:6]=[C:7]([N+:10]([O-:12])=[O:11])[CH:8]=[CH:9][C:4]=1[CH2:3][CH2:2][S:15]([CH3:14])(=[O:17])=[O:16]

Participants

4

Reactant 2

HCID 2733271Sodium methanesulfinateHCID 866721731-(2-Bromoethyl)-2-fluoro-4-nitrobenzene

Product 1

HCID 708167962-Fluoro-1-(2-(methylsulfonyl)ethyl)-4-nitrobenzeneYield 70.3%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
70 °C

Procedure

To a stirred solution of 1-(2-bromoethyl)-2-fluoro-4-nitrobenzene (1 g, 4.03 mmol) in isopropanol (15 mL) was added sodium methane sulfinate (2.05 g, 20.16 mmol) at room temperature. The reaction mixture was heated to 70° C. for 10 h. The reaction mixture was cooled to room temperature and was concentrated under reduced pressure to obtain a crude compound which was filtered out and the residue was washed with water (2×5 mL) to obtain pure 2-fluoro-1-(2-(methylsulfonyl)ethyl)-4-nitrobenzene (700 mg, 70%).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. concentrationwas concentrated under reduced pressure
  3. customto obtain a crude compound which
  4. filtrationwas filtered out
  5. washthe residue was washed with water (2×5 mL)

Sources & evidence

ORD record
ord-7c2e1282a6af45928fff9e62092d6166
Source dataset
uspto-grants-2015_02
Patent number
US08946204B2

Reaction notes

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