Benzyl Alcohol → 2-Benzyloxy-5-bromopyridine

HRID 1839159Notes

Reaction equation

HRID 1839159 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.[CH2:9]([OH:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[OH-].[K+].C1OCCOC2C(=CC=CC=2)OCCOCCOC2C(=CC=CC=2)OC1>C1(C)C=CC=CC=1.O>[CH2:9]([O:16][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

7

Reactant 4

HCID 244Benzyl AlcoholHCID 14797Potassium HydroxideHCID 26541Dibenzo-18-crown-6HCID 693532,5-Dibromopyridine

Product 1

HCID 111081912-Benzyloxy-5-bromopyridine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A mixture of 2,5-dibromopyridine, benzyl alcohol (1.3 eq), potassium hydroxide pellets (2.4 eq) and dibenzo-18-crown-6 (0.05 eq) in toluene (4 ml/mmol) was refluxed with azeotropic removal of water for 3 hours. After evaporation of the toluene, the resulting mixture was partitioned between chloroform and water. The crude product from the organic phase was recrystallized from ether-hexane to afford the 2-Benzyloxy-5-bromopyridine compound as a solid.

Workup

  1. customAfter evaporation of the toluene
  2. customthe resulting mixture was partitioned between chloroform and water
  3. customThe crude product from the organic phase was recrystallized from ether-hexane

Sources & evidence

ORD record
ord-0ab84277afc34d37a69b3a1109175b56
Source dataset
uspto-grants-2004_01
Patent number
US06677351B2

Reaction notes

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