p-Toluenesulfonic acid → 2-Bromo-5-(dimethoxymethyl)pyridine

HRID 885836Notes

Reaction equation

HRID 885836 reaction equation
[Br:1][C:2]1[N:7]=[CH:6][C:5](C=O)=[CH:4][CH:3]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH:21](OC)([O:24][CH3:25])[O:22][CH3:23].C([O-])(O)=O.[Na+]>CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:21]([O:24][CH3:25])[O:22][CH3:23])=[CH:6][N:7]=1

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 9005Trimethyl orthoformateHCID 516892Sodium BicarbonateHCID 117692346-Bromo-3-pyridinecarboxaldehyde

Product 1

HCID 64252132-Bromo-5-(dimethoxymethyl)pyridineYield 95.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 6-bromopyridine-3-carbaldehyde (3.07 g, 16.5 mmol), p-toluenesulfonic acid (386 mg, 2.02 mmol) and trimethyl orthoformate (1.97 ml, 18 mmol) in MeOH (80 ml) was stirred at room temperature for 48 hours. The mixture was then brought to basic conditions with a 5% NaHCO3 solution and extracted twice with diethyl ether. The pooled organic phases were dried over Na2SO4 and evaporated to dryness to give 3.66 g of 2-bromo-5-dimethoxymethyl-pyridine as a pale yellow oil.

Workup

  1. extractionextracted twice with diethyl ether
  2. dry with materialThe pooled organic phases were dried over Na2SO4
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-da5f42b359da4c28b399296303b378bb
Source dataset
uspto-grants-2012_08
Patent number
US08242175B2

Reaction notes

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