Water → 3-((Naphthalen-6-YL)methoxy)-5-bromopyridine

HRID 1614232Notes

Reaction equation

HRID 1614232 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][OH:12].[H-].[Na+].[Br:15][C:16]1[CH:17]=[N:18][CH:19]=[C:20](Br)[CH:21]=1.O>CN(C)C=O>[Br:15][C:16]1[CH:17]=[N:18][CH:19]=[C:20]([O:12][CH2:11][C:2]2[CH:3]=[CH:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH:1]=2)[CH:21]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 693693,5-DibromopyridineHCID 741282-Naphthalenemethanol

Product 1

HCID 197730563-((Naphthalen-6-YL)methoxy)-5-bromopyridineYield 44.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 2-naphthylmethanol (1.58 g) in dimethylformamide (20 ml) was added to a slurry of sodium hydride (55% w/w dispersion in oil, 0.48 g) in dimethylformamide (2 ml) and the mixture was stirred at ambient temperature for 20 minutes. 3,5-Dibromopyridine (2.37 g) was added and the solution was heated to 120° C. for 5 hours and then allowed to stand at ambient temperature overnight. The mixture was poured into water (160 ml) and extracted with ethyl acetate (3×50 ml). The combined extracts were washed with water, dried (MgSO4) and evaporated. The residue was purified by column chromatography eluting with increasingly polar mixtures of petrol (b.p. 60°-80° C.) and ethyl acetate to give 3-bromo-5-(naphth-2-ylmethoxy)pyridine (1.4 g), m.p. 108°-109° C.

Workup

  1. temperaturethe solution was heated to 120° C. for 5 hours
  2. waitto stand at ambient temperature overnight
  3. extractionextracted with ethyl acetate (3×50 ml)
  4. washThe combined extracts were washed with water
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customThe residue was purified by column chromatography
  8. washeluting
  9. temperaturewith increasingly polar mixtures of petrol (b.p. 60°-80° C.) and ethyl acetate

Sources & evidence

ORD record
ord-5c845560677f4b6ba2ec0cc37d22748a
Source dataset
uspto-grants-1993_03
Patent number
US05196422

Reaction notes

Loading…