2-Fluoropyridine → 2-((4-Bromobenzyl)oxy)pyridine

HRID 1807424Notes

Reaction equation

HRID 1807424 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[Br:8][C:9]1[CH:16]=[CH:15][C:12]([CH2:13][OH:14])=[CH:11][CH:10]=1.CC(C)([O-])C.[K+].CN1CCCC1=O>O>[Br:8][C:9]1[CH:16]=[CH:15][C:12]([CH2:13][O:14][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=2)=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 97462-FluoropyridineHCID 13387N-methyl-2-pyrrolidoneHCID 701194-Bromobenzyl alcoholHCID 23665647Potassium tert-butoxide

Product 1

HCID 247991602-((4-Bromobenzyl)oxy)pyridine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-fluoropyridine (1.6 g), 4-bromobenzyl alcohol (3.08 g), potassium tert-butoxide (2.03 g) and N-methylpyrrolidone (12.8 ml) was heated at 100° C. by microwave irradiation for one minute. The mixture was diluted with water and extracted with ethyl acetate. The organic phase was dried over magnesium sulfate, filtered and concentrated. 2-(4-Bromobenzyloxy)pyridine was obtained in this way.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic phase was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-66b9e6ac2b9d4371b8dde53807c78ca6
Source dataset
uspto-grants-2013_01
Patent number
US08357686B2

Reaction notes

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