Toluene → 2-Benzyloxy-6-bromopyridine

HRID 322063

Reaction equation

HRID 322063 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[N:3]=1.[OH-:9].[K+].[C:11]1([CH3:17])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C1OCCOCCOCCOCCOCCOC1>[CH2:17]([O:9][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[N:3]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 122742,6-DibromopyridineHCID 14797Potassium Hydroxide

Product 1

HCID 8174752-Benzyloxy-6-bromopyridine

Reagents, catalysts & solvents 1

HCID 2855718-Crown-6Catalyst

Procedure

A stirred mixture of 2,6-dibromopyridine (3.55 g), benzyl. alcohol (1.63 g), potassium hydroxide (1.68 g), 18-Crown-6 (0.20 g) and toluene (25 ml) is heated under reflux for 30 minutes. The cool solution washed with water and brine, dried (MgSO4) and evaporated to give an oil which is vacuum-distilled (Kugelrohr) to give 3.85 g of 2-benzyloxy-6-bromopyridine, bp 220-225° C./1.0 mm.

Workup

  1. temperatureunder reflux for 30 minutes
  2. washThe cool solution washed with water and brine
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customto give an oil which
  6. distillationis vacuum-distilled (Kugelrohr)

Sources & evidence

ORD record
ord-93682894d27b42bb9ad767ec95113533
Source dataset
uspto-grants-2001_04
Patent number
US06211220B1

Linked notes

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