Reaction #417949

Reaction equation

5-bromo-2-fluoropyridine

cyclopropane methanol

NaH

→

5-Bromo-2-cyclopropylmethoxy-pyridine

Solvents

THF

Conditions

Workup

1. 1
   workup.STIRRINGthe mixture is stirred at r.t. over night
2. 2
   OtherThe reaction is quenched by the addition of water
3. 3
   Extractionextracted with EtOAc
4. 4
   Dryingdried over MgSO4
5. 5
   Filtrationfiltered
6. 6
   Otherthe solvent is removed in vacuo
7. 7
   OtherThe crude product is purified by HPLC (MeOH/H2O/FA)

Procedure

0.49 g (6.82 mmol) cyclopropane methanol in 10 mL THF are charged with 0.42 g (11.4 mmol) NaH and the reaction mixture is stirred at r.t. for 20 min. Then 1.00 g (5.68 mmol) 5-bromo-2-fluoropyridine are added and the mixture is stirred at r.t. over night. The reaction is quenched by the addition of water and extracted with EtOAc. The organic layers are combined, dried over MgSO4, filtered and the solvent is removed in vacuo. The crude product is purified by HPLC (MeOH/H2O/FA).

Source