Benzyl Alcohol → 2-Benzyloxy-5-bromopyridine

HRID 860995Notes

Reaction equation

HRID 860995 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+]>C1(C)C=CC=CC=1>[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

5

Reactant 3

HCID 244Benzyl AlcoholHCID 14797Potassium HydroxideHCID 693532,5-Dibromopyridine

Product 1

HCID 111081912-Benzyloxy-5-bromopyridine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 2,5-dibromopyridine (1.0 eq.), benzyl alcohol (1.3 eq.), KOH (2.4 eq.) and DB-18—C-6 (0.0 Seq.) in toluene (0.3M) was refluxed for 3 h, then stirred overnight at rt. The mixture was concentrated, poured in water and extracted with Tol (2×). The combined organic extracts were dried over MgSO4, filtered and concentrated. Recrystallization in Hex:Et2O afforded the title compound as a white solid.

Workup

  1. temperaturewas refluxed for 3 h
  2. concentrationThe mixture was concentrated
  3. additionpoured in water
  4. extractionextracted with Tol (2×)
  5. dry with materialThe combined organic extracts were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customRecrystallization in Hex

Sources & evidence

ORD record
ord-6ff666849f224191a29269fd96a3ea6e
Source dataset
uspto-grants-2006_12
Patent number
US07153968B2

Reaction notes

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