Potassium Hydroxide → 4-Bromo-2-chloromethyl-3,5-dimethylpyridine

HRID 857933Notes

Reaction equation

HRID 857933 reaction equation
[Cl:1][CH2:2][C:3]1[C:8]([CH3:9])=[C:7](O)[C:6]([CH3:11])=[CH:5][N:4]=1.P(Br)(Br)([Br:14])=O.[OH-].[K+]>C(Cl)(Cl)Cl>[Br:14][C:7]1[C:6]([CH3:11])=[CH:5][N:4]=[C:3]([CH2:2][Cl:1])[C:8]=1[CH3:9]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 24613Phosphorus oxybromideHCID 178430506HCID 178430506, compound

Product 1

HCID 167363514-Bromo-2-chloromethyl-3,5-dimethylpyridineYield 78%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 2-chloromethyl-3,5-dimethyl-pyridin-4-ol (8.2 g, 47.8 mmol) and POBr3 (60 g, 209 mmol) was stirred at 130° C. for 3 h. The resulting viscous oil was cooled to r.t. and poured onto ice water. The pH was adjusted to 10 with solid KOH. Work-up (CHCl3), drying (MgSO4) and evaporation afforded the title compound as a purple solid (8.7 g, 78% yield) which was used without purification. R.t.: 6.03 min. 1H-NMR (CDCl3): 8.20 (s, 1H), 4.62 (s, 2H), 2.50 (s, 3H), 2.38 (s, 3H).

Workup

  1. temperatureThe resulting viscous oil was cooled to r.t.
  2. additionpoured onto ice water
  3. customdrying
  4. custom(MgSO4) and evaporation

Sources & evidence

ORD record
ord-1d621cc8ae9c4a7d8dd9a25c4eda273e
Source dataset
uspto-grants-2006_12
Patent number
US07148228B2

Reaction notes

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