Sodium methanesulfinate → 8-Bromo-6-[(methanesulfonyl)methyl]quinoline

HRID 896650Notes

Reaction equation

HRID 896650 reaction equation
Br[CH2:2][C:3]1[CH:4]=[C:5]2[C:10](=[C:11]([Br:13])[CH:12]=1)[N:9]=[CH:8][CH:7]=[CH:6]2.[CH3:14][S:15]([O-:17])=[O:16].[Na+]>CN(C=O)C>[Br:13][C:11]1[CH:12]=[C:3]([CH2:2][S:15]([CH3:14])(=[O:17])=[O:16])[CH:4]=[C:5]2[C:10]=1[N:9]=[CH:8][CH:7]=[CH:6]2

Participants

4

Reactant 2

HCID 2733271Sodium methanesulfinateHCID 155413198-Bromo-6-(bromomethyl)quinoline

Product 1

HCID 98793738-Bromo-6-[(methanesulfonyl)methyl]quinoline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
21 °C

Procedure

To a solution of 6-bromomethyl-8-bromoquinoline (60 g, 200 mmol, described in International Patent Publication WO 94/22852) in DMF (500 mL) was added sodium methanesulfinate (27.6 g, 270 mmol). After stirring overnight at 21° C., the mixture was quenched with H2O (2L), stirred for 1 h, isolated by filtration, and washed with Et2O to yield the 8-Bromo-6-methanesulfonylmethyl-quinoline as a white solid.

Workup

  1. customthe mixture was quenched with H2O (2L)
  2. stirringstirred for 1 h
  3. customisolated by filtration
  4. washwashed with Et2O

Sources & evidence

ORD record
ord-2c8f24113cec4e7b91e6bf91abbb5911
Source dataset
uspto-grants-2005_07
Patent number
US06919353B2

Reaction notes

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