Dichloromethane → 2-Methyl-3-nitrobenzyl methanesulfonate

HRID 1436854Notes

Reaction equation

HRID 1436854 reaction equation
[CH3:1][C:2]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][OH:5].ClCCl.C(N(CC)CC)C.[S:23](Cl)([CH3:26])(=[O:25])=[O:24]>O>[CH3:26][S:23]([O:5][CH2:4][C:3]1[CH:6]=[CH:7][CH:8]=[C:9]([N+:10]([O-:12])=[O:11])[C:2]=1[CH3:1])(=[O:25])=[O:24]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 902892-Methyl-3-nitrobenzyl alcohol

Product 1

HCID 193697582-Methyl-3-nitrobenzyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
5 °C

Procedure

200 g 2-Methyl-3-nitro benzylalcohol is added to dichloromethane (2000 ml) and triethylamine (250 ml). Mesyl chloride is added drop wise while maintaining temperature between 0-10° C. and stirred until the completion of reaction. It is further stirred 2 hours at room temperature. Water is added to the reaction mixture and stirred for 10 minutes. Organic layer was separated and washed with brine. Dichloromethane was evaporated to yield the oily brown 2-Methyl-3-nitrobenzyl methanesulfonate (207-210 g).

Workup

  1. stirringstirred for 10 minutes
  2. customOrganic layer was separated
  3. washwashed with brine
  4. customDichloromethane was evaporated

Sources & evidence

ORD record
ord-1ad5c504a8ef4d32867a9aa8a945ff6c
Source dataset
uspto-grants-2009_11
Patent number
US07619095B2

Reaction notes

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