Reaction #417952

Reaction equation

dimethyl sulfone

sodium-bis-(trimethylsilyl)-amide

THF

2-bromo-6-fluoropyridine

→

2-Bromo-6-(1-methanesulfonyl-cyclopropyl)-pyridine

Conditions

Workup

1. 1
   OtherThe reaction is quenched by the addition
2. 2
   ExtractionNaCl solution and extracted with EtOAc
3. 3
   DryingThe organic layer is dried over MgSO4
4. 4
   Filtrationfiltered
5. 5
   Otherthe solvent is removed in vacuo

Procedure

Under inert gas atmosphere 28.4 mL (56.8 mmol) of a sodium-bis-(trimethylsilyl)-amide solution in THF (c=2 mol/L) are chilled to −17° C. and dropwise charged with 2.00 g (11.3 mmol) 2-bromo-6-fluoropyridine. Afterwards 2.14 g (22.7 mmol) dimethyl sulfone are added and the reaction mixture is stirred at −17° C. for 1 h. The reaction is quenched by the addition of aq. sat.NaCl solution and extracted with EtOAc. The organic layer is dried over MgSO4, filtered and the solvent is removed in vacuo.

Source