Hydrogen Bromide → 2-(Bromomethyl)-6-methylpyridine

HRID 1471284Notes

Reaction equation

HRID 1471284 reaction equation
[BrH:1].S(=O)(=O)(O)O.[CH3:7][C:8]1[N:13]=[C:12]([CH2:14]O)[CH:11]=[CH:10][CH:9]=1>O>[Br:1][CH2:14][C:12]1[CH:11]=[CH:10][CH:9]=[C:8]([CH3:7])[N:13]=1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 1118Sulfuric AcidHCID 707366-Methyl-2-pyridylmethanol

Product 1

HCID 125437332-(Bromomethyl)-6-methylpyridine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a flask containing a mixture of 15 ml of 48% hydrobromic acid and 11 ml of sulfuric acid was added 5 g of 6-methyl-2-pyridinemethanol dropwise under nitrogen. The mixture was heated to 90 C for 4 hours, and poured into 25 ml of water. After neutralization with sodium carbonate, the product was extracted with 100 ml ethyl acetate and washed with 30 ml of water. Following solvent removal, the product was purified by silica gel chromatography using 25% ethyl acetate in hexane, resulting in 6.3 g of a pink oil which solidified on storage at −5 C.

Workup

  1. additionTo a flask containing
  2. temperatureThe mixture was heated to 90 C for 4 hours
  3. extractionAfter neutralization with sodium carbonate, the product was extracted with 100 ml ethyl acetate
  4. washwashed with 30 ml of water
  5. customFollowing solvent removal
  6. customthe product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-69ad25a92b3b41bf8e3744303a46c536
Source dataset
uspto-grants-2015_04
Patent number
US09011734B2

Reaction notes

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