Water → 2-Benzyloxy-4-methylsulfanylmethyl-1-nitrobenzene

HRID 660687Notes

Reaction equation

HRID 660687 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([CH2:15]Br)[CH:12]=[CH:11][C:10]=1[N+:17]([O-:19])=[O:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:20][S-:21].[Na+].O>CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([CH2:15][S:21][CH3:20])[CH:12]=[CH:11][C:10]=1[N+:17]([O-:19])=[O:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4378561Sodium methanethiolateHCID 621150422-Benzyloxy-4-bromomethyl-1-nitrobenzene

Product 1

HCID 688400562-Benzyloxy-4-methylsulfanylmethyl-1-nitrobenzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-benzyloxy-4-bromomethyl-1-nitrobenzene (Example 83, step C) (1.0 g, 3.1 mmol) in 20 mL DMF is added sodium thiomethoxide (228 mg, 3.26 mmol). The solution is stirred at RT for 2 h then water is added and the mixture is extracted with EtOAc. The organic layer is washed with water and brine, and dried over sodium sulfate. The solvent is removed under reduced pressure to give the title compound as a yellow liquid.

Workup

  1. extractionthe mixture is extracted with EtOAc
  2. washThe organic layer is washed with water and brine
  3. dry with materialdried over sodium sulfate
  4. customThe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-fed2503a03e94ff38799cecb1e66a9aa
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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