2-(Bromomethyl)-1-methoxy-4-nitrobenzene → 1-Methoxy-2-methylsulfanylmethyl-4-nitrobenzene

HRID 47439Notes

Reaction equation

HRID 47439 reaction equation
[CH3:1][S-:2].[Na+].[CH3:4][O:5][C:6]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][C:7]=1[CH2:8]Br>CN(C)C=O>[CH3:4][O:5][C:6]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][C:7]=1[CH2:8][S:2][CH3:1]

Participants

4

Reactant 2

HCID 775162-(Bromomethyl)-1-methoxy-4-nitrobenzeneHCID 4378561Sodium methanethiolate

Product 1

HCID 227451381-Methoxy-2-methylsulfanylmethyl-4-nitrobenzeneYield 92.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium thiomethoxide (0.469 g) was added to a solution of 2-methoxy-5-nitrobenzyl bromide (1.5 g) in dimethylformamide (25 ml). The mixture was stirred for 16 h, solvent removed at reduced pressure and the residue dissolved in ethyl acetate and washed with water and brine, dried (Na2SO4) and solvent removed at reduced pressure to give the title compound (1.2 g) as a yellow solid

Workup

  1. customsolvent removed at reduced pressure
  2. dissolutionthe residue dissolved in ethyl acetate
  3. washwashed with water and brine
  4. dry with materialdried (Na2SO4) and solvent
  5. customremoved at reduced pressure

Sources & evidence

ORD record
ord-7bea43754b4d4147850944721591ef26
Source dataset
uspto-grants-2004_03
Patent number
US06699879B1

Reaction notes

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