alpha-Chloro-m-nitrotoluene → Methyl(3-nitrobenzyl)sulfane

HRID 1405168Notes

Reaction equation

HRID 1405168 reaction equation
[CH3:1][S-:2].[Na+].Cl[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([N+:12]([O-:14])=[O:13])[CH:7]=1>C(O)C>[CH3:1][S:2][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([N+:12]([O-:14])=[O:13])[CH:7]=1

Participants

4

Reactant 2

HCID 12078alpha-Chloro-m-nitrotolueneHCID 4378561Sodium methanethiolate

Product 1

HCID 22031873Methyl(3-nitrobenzyl)sulfaneYield 100.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium methanethiolate (13.5 g; 192 mmol) was added in two portions to a stirred solution of 1-(chloromethyl)-3-nitrobenzene (30.0 g; 175 mmol) in ethanol (360 ml) at −15° C. The cold bath was removed and the batch was stirred at room temperature for 3 hours. The batch was diluted with brine and extracted with ethyl acetate (2×). The combined organic phases were washed with water, dried (sodium sulfate), filtered and concentrated to give the desired product (32.2 g) that was used without further purification.

Workup

  1. customThe cold bath was removed
  2. additionThe batch was diluted with brine
  3. extractionextracted with ethyl acetate (2×)
  4. washThe combined organic phases were washed with water
  5. dry with materialdried (sodium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-ecfd755aec5149de8f1d24dac301030c
Source dataset
uspto-grants-2014_12
Patent number
US08916557B2

Reaction notes

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