Benzyl Alcohol → 2-Benzyloxy-5-bromopyridine

HRID 1177745Notes

Reaction equation

HRID 1177745 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.C1OCCOC2C(=CC=CC=2)OCCOCCOC2C(=CC=CC=2)OC1.[CH2:35]([OH:42])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.[OH-].[K+]>C1(C)C=CC=CC=1>[CH2:35]([O:42][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

6

Reactant 4

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

Product 1

HCID 111081912-Benzyloxy-5-bromopyridine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A suspension of 2,5-dibromopyridine (2.0 g, 8.4 mmol), dibenzo-18-crown-6 (0.14 g, 0.05 equiv), benzyl alcohol (1.1 mL, 1.3 equiv), and potassium hydroxide (1.1 g, 2.4 equiv) in toluene (30 mL) were heated at reflux for 3 h in an apparatus fitted with a Dean-Stark trap. The suspension was cooled, concentrated, suspended in water, and extracted into methylene chloride. The combined organic phases were washed with water, then brine, dried over magnesium sulfate, and concentrated to give 1.9 g (85%) which was used without purification. Mass spec.: 264.25 (MH)+.

Workup

  1. temperaturewere heated
  2. temperatureat reflux for 3 h in an apparatus
  3. customfitted with a Dean-Stark trap
  4. temperatureThe suspension was cooled
  5. concentrationconcentrated
  6. extractionextracted into methylene chloride
  7. washThe combined organic phases were washed with water
  8. dry with materialbrine, dried over magnesium sulfate
  9. concentrationconcentrated
  10. customto give 1.9 g (85%) which
  11. customwas used without purification

Sources & evidence

ORD record
ord-951610c775354a399f1c5195c7febedf
Source dataset
uspto-grants-2010_11
Patent number
US07842808B2

Reaction notes

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