Benzene, 1-(bromomethyl)-3-nitro- → 1-(Methanesulfonylmethyl)-3-nitrobenzene

HRID 1890989Notes

Reaction equation

HRID 1890989 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([N+:9]([O-:11])=[O:10])[CH:4]=1.[CH3:12][S:13]([O-:15])=[O:14].[Na+]>C(O)C>[CH3:12][S:13]([CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([N+:9]([O-:11])=[O:10])[CH:4]=1)(=[O:15])=[O:14]

Participants

4

Reactant 2

HCID 77568Benzene, 1-(bromomethyl)-3-nitro-HCID 2733271Sodium methanesulfinate

Product 1

HCID 179084331-(Methanesulfonylmethyl)-3-nitrobenzeneYield 87%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of 1-bromomethyl-3-nitro-benzene (5.0 g, 23 mmol) in ethanol (50 mL) was added solution of sodium methanesulfinate (3.06 g, 30 mmol) in ethanol (30 mL) and the mixture was stirred for 4 h at room temperature, then was concentrated in vacuo to volume about 20 mL and diluted with water (200 mL). Formed precipitate was filtered out, washed with water (2×100 mL) and dried to give 1-methanesulfonylmethyl-3-nitro-benzene (4.3 g; 87%) as yellowish crystalline powder.

Workup

  1. concentrationwas concentrated in vacuo to volume about 20 mL
  2. additiondiluted with water (200 mL)
  3. customFormed precipitate
  4. filtrationwas filtered out
  5. washwashed with water (2×100 mL)
  6. customdried

Sources & evidence

ORD record
ord-e1958774d3c341d2898c365c7e60fbaa
Source dataset
uspto-grants-2013_08
Patent number
US08507498B2

Reaction notes

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