4-Methoxybenzyl alcohol → 5-Bromo-2-[(4-methoxyphenyl)methoxy]pyridine

HRID 1173448Notes

Reaction equation

HRID 1173448 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.[CH3:9][O:10][C:11]1[CH:12]=[CH:13][C:14]([CH2:17][OH:18])=[CH:15][CH:16]=1>>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([O:18][CH2:17][C:14]2[CH:13]=[CH:12][C:11]([O:10][CH3:9])=[CH:16][CH:15]=2)=[N:3][CH:4]=1

Participants

3

Reactant 2

HCID 77384-Methoxybenzyl alcoholHCID 693532,5-Dibromopyridine

Product 1

HCID 269670665-Bromo-2-[(4-methoxyphenyl)methoxy]pyridine

Procedure

Synthesized as described in Example 53A from 2,5-dibromopyridine and p-methoxybenzyl alcohol with the following exceptions: the reaction was heated at reflux for 90 min, and the title compound was purified by flash chromatography (EtOAc/hexanes): 1H NMR (400 MHz, CDCl3) δ 8.21 (dd, J=2.6, 0.6 Hz, 1H), 7.64 (dd, J=8.8, 2.6 Hz, 1H), 7.38 (m, 2H, AA′XX′), 6.91 (m, 2H, AA′XX′), 6.69 (dd, J=8.9, 0.6 Hz, 1H), 5.26 (s, 2H), 3.81 (s, 3H).

Workup

  1. customSynthesized
  2. temperaturethe reaction was heated
  3. temperatureat reflux for 90 min
  4. customthe title compound was purified by flash chromatography (EtOAc/hexanes)

Sources & evidence

ORD record
ord-3652b48e264f48d198e31e4663c5210c
Source dataset
uspto-grants-2010_11
Patent number
US07834063B2

Reaction notes

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