Methanesulfonyl chloride → 2-(3-Nitro-benzenesulfonyl)ethyl methanesulfonate

HRID 914995Notes

Reaction equation

HRID 914995 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([S:10]([CH2:13][CH2:14][OH:15])(=[O:12])=[O:11])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[CH3:16][S:17](Cl)(=[O:19])=[O:18]>ClCCl.N1C=CC=CC=1>[CH3:16][S:17]([O:15][CH2:14][CH2:13][S:10]([C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)(=[O:12])=[O:11])(=[O:19])=[O:18]

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 170561Ethanol, 2-[(3-nitrophenyl)sulfonyl]-

Product 1

HCID 589580692-(3-Nitro-benzenesulfonyl)ethyl methanesulfonateYield 71.5%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(3-nitrobenzenesulfonyl)ethanol (101) (5.0 g, 21.6 mmol) in dichloromethane (31.5 mL) and pyridine (7 mL) was added methanesulfonyl chloride (4.9 g, 43 mmol). The mixture was stirred at room temperature overnight before it was partitioned between dichloromethane (200 mL) and 0.5 N HCl (200 mL). The organic layer was dried over MgSO4 and concentrated on a rotavap to give 102 (4.78 g, 71%).

Workup

  1. customwas partitioned between dichloromethane (200 mL) and 0.5 N HCl (200 mL)
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated on a rotavap

Sources & evidence

ORD record
ord-08464b2f7870468fa69c150e600cc333
Source dataset
uspto-grants-2007_09
Patent number
US07265122B2

Reaction notes

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