Water → HCID 67173101, compound

HRID 1256099Notes

Reaction equation

HRID 1256099 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[CH2:11][CH2:12][O:13][CH3:14].C([O-])([O-])=O.[Cs+].[Cs+].[CH2:21]([SH:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.O>CN(C=O)C>[CH2:21]([S:28][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[CH2:11][CH2:12][O:13][CH3:14])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7509Benzyl mercaptanHCID 10796Cesium carbonateHCID 67172881HCID 67172881, compound

Product 1

HCID 67173101HCID 67173101, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-bromo-2-(2-methoxyethyl)-4-nitrobenzene (7.8 g, 30 mmol) and Cs2CO3 (14.66 g, 45 mmol) in DMF (100 mL) was added BnSH (4.1 g, 33 mmol) slowly, followed by stirring at room temperature for three hours. Water was added, the precipitate was filtered, washed by water and petroleum to give benzyl(2-(2-methoxyethyl)-4-nitrophenyl)sulfane (8 g, yield 88%). 1H NMR: 400 MHz CDCl3 δ 8.05 (s, 1H), 8.01-7.98 (m, 1H), 7.38-7.28 (m, 6H), 4.23 (s, 2H), 3.64-3.61 (m, 2H), 3.34 (s, 3H), 3.03-2.99 (m, 2H).

Workup

  1. filtrationthe precipitate was filtered
  2. washwashed by water and petroleum

Sources & evidence

ORD record
ord-c6ccddc512c84a20bd54253a55370517
Source dataset
uspto-grants-2013_06
Patent number
US08461134B2

Reaction notes

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