Benzyl Alcohol → 2-(Benzyloxy)-4-bromopyridine

HRID 337668Notes

Reaction equation

HRID 337668 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4](F)[CH:3]=1.[CH2:9]([OH:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C1OCCOC2C(=CC=CC=2)OCCOCCOC2C(=CC=CC=2)OC1.[OH-].[K+]>C1(C)C=CC=CC=1>[CH2:9]([O:16][C:4]1[CH:3]=[C:2]([Br:1])[CH:7]=[CH:6][N:5]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 14797Potassium HydroxideHCID 26541Dibenzo-18-crown-6HCID 27628514-Bromo-2-fluoropyridine

Product 1

HCID 532173892-(Benzyloxy)-4-bromopyridine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 4-bromo-2-fluoropyridine (1 eq.), benzyl alcohol (1.2 eq.) and dibenzo-18-crown-6 (0.05 eq.) in toluene (0.4 M) was added potassium hydroxide (2 eq.). A Dean-Stark apparatus was then attached and the reaction suspension was heated at reflux for 3 h. After cooling to RT, the reaction mixture was diluted with hexanes and then filtered through a pad of celite. Concentration of the filtrate in vacuo afforded a yellow oil. Purification of the crude product thus obtained by way of column chromatography (SiO2, 97:3 (v/v) Hex:Et2O) afforded the title compound as a colorless oil.

Workup

  1. temperaturethe reaction suspension was heated
  2. temperatureat reflux for 3 h
  3. filtrationfiltered through a pad of celite
  4. customConcentration of the filtrate in vacuo afforded a yellow oil
  5. customPurification of the crude product
  6. customthus obtained by way of column chromatography (SiO2, 97:3 (v/v) Hex:Et2O)

Sources & evidence

ORD record
ord-7a433f85a7034bbf8e7e653ec0246a56
Source dataset
uspto-grants-2014_11
Patent number
US08889714B2

Reaction notes

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