Water → 2-(4-Methanesulfonamidophenoxy)ethyl bromide

HRID 1106861Notes

Reaction equation

HRID 1106861 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][C:7]([O:8][CH2:9][CH2:10][Br:11])=[CH:6][CH:5]=1)([O-])=O.[CH3:14][S:15](Cl)(=[O:17])=[O:16].O>CO.[H][H].[Pd]>[CH3:14][S:15]([NH:1][C:4]1[CH:13]=[CH:12][C:7]([O:8][CH2:9][CH2:10][Br:11])=[CH:6][CH:5]=1)(=[O:17])=[O:16]

Participants

7

Reactant 3

HCID 962WaterHCID 31297Methanesulfonyl chlorideHCID 2359871-(2-Bromoethoxy)-4-nitrobenzene

Product 1

HCID 111091562-(4-Methanesulfonamidophenoxy)ethyl bromideYield 36.8%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 178418361HCID 178418361, compoundSolvent

Procedure

2-(4-nitrophenoxy)ethyl bromide (0.5 g, 2.03 mmol) was dissolved in methanol (30 ml) and, after adding 10% Pd/C (0.2 g), the solution was stirred for 1 h in hydrogen gas, followed by filtration. The filtrate was concentrated under vacuum and the residue was dissolved in pyridine (20 ml). To the resulting solution, methanesulfonyl chloride (0.25 ml, 3.2 mmol) was slowly added dropwise, followed by stirring overnight. Water was poured into the reaction mixture, followed by extraction with ethyl acetate and concentration under vacuum. The residue was subjected to column chromatography using a 1:1 solvent system of ethyl acetate and hexane as an eluent to yield the end compound 2-(4-methanesulfonamidophenoxy)ethyl bromide (0.22 g).

Workup

  1. filtrationfollowed by filtration
  2. concentrationThe filtrate was concentrated under vacuum
  3. dissolutionthe residue was dissolved in pyridine (20 ml)
  4. extractionfollowed by extraction with ethyl acetate and concentration under vacuum

Sources & evidence

ORD record
ord-f34ed35b3e624d1fa38ff3bc2d0f16d2
Source dataset
uspto-grants-2000_05
Patent number
US06057358

Reaction notes

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