4-Nitrobenzyl bromide → 1-(Methanesulfonylmethyl)-4-nitrobenzene

HRID 885914Notes

Reaction equation

HRID 885914 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8]Br)=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH3:12][S:13]([O-:15])=[O:14].[Na+]>CN(C=O)C>[CH3:12][S:13]([CH2:8][C:7]1[CH:10]=[CH:11][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1)(=[O:15])=[O:14]

Participants

4

Reactant 2

HCID 660114-Nitrobenzyl bromideHCID 2733271Sodium methanesulfinate

Product 1

HCID 2873701-(Methanesulfonylmethyl)-4-nitrobenzeneYield 75.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

To a stirred solution of 4-nitrobenzyl bromide (10.0 g, 46.3 mmol) in DMF (25 mL) was added sodium methanesulfinate (7.1 g, 69.4 mmol). The reaction mixture was stirred at 65° C. for 30 minutes, and then partitioned between water (30 mL) and EtOAc (30 mL). The organic fraction was separated, washed with water (2×30 ml), dried (Na2SO4), filtered and concentrated in vacuo to give the title compound (7.5 g, 75%) as a yellow solid that was used without further purification. δH (DMSO-d6) 8.28 (2H, d, J 8.8 Hz), 7.70 (2H, d, J 8.8 Hz), 4.72 (2H, s), 2.97 (3H, s).

Workup

  1. custompartitioned between water (30 mL) and EtOAc (30 mL)
  2. customThe organic fraction was separated
  3. washwashed with water (2×30 ml)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b147a0fcc7e64cb0bc6aaa54d6a784a6
Source dataset
uspto-grants-2012_08
Patent number
US08242116B2

Reaction notes

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