Hydrogen Bromide → 5-(Bromomethyl)-2-o-tolylpyridine hydrobromide

HRID 2422368Notes

Reaction equation

HRID 2422368 reaction equation
[C:1]1([CH3:15])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[N:12]=[CH:11][C:10]([CH2:13]O)=[CH:9][CH:8]=1.[BrH:16]>>[BrH:16].[Br:16][CH2:13][C:10]1[CH:9]=[CH:8][C:7]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=2[CH3:15])=[N:12][CH:11]=1

Participants

3

Reactant 2

HCID 260Hydrogen BromideHCID 24729916(6-o-Tolylpyridin-3-yl)methanol

Product 1

HCID 672435665-(Bromomethyl)-2-o-tolylpyridine hydrobromideYield 95%

Procedure

A solution of 4.49 g (22.5 mmol) of (6-o-tolylpyridin-3-yl)methanol in 75 mL of 48% hydrobromic acid was heated to reflux for 64 h. The reaction mixture was partially cooled and excess hydrobromic acid was removed by vacuum distillation (110° C.@2 Torr) until a tan solid residue remained in the flask. Distillation was carried out using a large KOH pellet trap placed between the distillation apparatus and the vacuum pump. The solid residue was slurried in diethyl ether, filtered and dried under a nitrogen stream to give 7.38 g of product, 95% yield.

Workup

  1. temperatureto reflux for 64 h
  2. temperatureThe reaction mixture was partially cooled
  3. customexcess hydrobromic acid was removed by vacuum distillation (110° C.@2 Torr) until a tan solid residue
  4. distillationDistillation
  5. filtrationfiltered
  6. customdried under a nitrogen stream

Sources & evidence

ORD record
ord-f188de5c926b45cfb869d180bea49ba1
Source dataset
uspto-grants-2011_06
Patent number
US07960349B2

Reaction notes

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