Benzyl Bromide → 2-(Benzyloxy)-3-bromo-5-chloropyridine

HRID 1828762Notes

Reaction equation

HRID 1828762 reaction equation
[Br:1][C:2]1[C:3]([OH:9])=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1.[CH2:10](Br)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C1C=CC=CC=1.C(=O)([O-])[O-].[Ag+2]>[CH2:10]([O:9][C:3]1[C:2]([Br:1])=[CH:7][C:6]([Cl:8])=[CH:5][N:4]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 2

HCID 7498Benzyl BromideHCID 178517755HCID 178517755, compound

Product 1

HCID 220583822-(Benzyloxy)-3-bromo-5-chloropyridine

Reagents, catalysts & solvents 2

HCID 178418647HCID 178418647, compoundCatalystHCID 241BenzeneSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 3-bromo-5-chloro-2-hydroxypyridine (81 g), benzyl bromide (52 mL) and silver carbonate (97 g) in benzene (1 L) was heated at 70° C. for 1 h. The mixture was cooled to r.t. and then filtered through a bed of celite. The filtrate was concentrated and the residual off-white solid was recrystallized from hexane to provide the title compound as a white solid (102 g).

Workup

  1. temperatureThe mixture was cooled to r.t.
  2. filtrationfiltered through a bed of celite
  3. concentrationThe filtrate was concentrated
  4. customthe residual off-white solid was recrystallized from hexane

Sources & evidence

ORD record
ord-b64d795333414b6db576e6b25eca4292
Source dataset
uspto-grants-2006_06
Patent number
US07060715B2

Reaction notes

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