Trimethyl orthoformate → 2-Bromo-5-(dimethoxymethyl)pyridine

HRID 556287Notes

Reaction equation

HRID 556287 reaction equation
[CH:1](OC)([O:4][CH3:5])[O:2][CH3:3].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[Br:20][C:21]1[N:26]=[CH:25][C:24](C=O)=[CH:23][CH:22]=1>CO>[Br:20][C:21]1[CH:22]=[CH:23][C:24]([CH:1]([O:4][CH3:5])[O:2][CH3:3])=[CH:25][N:26]=1

Participants

5

Reactant 3

HCID 9005Trimethyl orthoformateHCID 521998p-Toluenesulfonic acid monohydrateHCID 117692346-Bromo-3-pyridinecarboxaldehyde

Product 1

HCID 64252132-Bromo-5-(dimethoxymethyl)pyridineYield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Trimethyl orthoformate (643 μl, 5.9 mmol) and p-toluene sulphonic acid monohydrate (102 mg, 0.54 mmol) were added to 6-bromo-pyridine-3-carbaldehyde (1 g, 5.37 mmol) dissolved in MeOH (40 ml). The mixture was stirred for 24 h at room temperature and then partitioned between water and Et2O. The organic extract was washed with water, 5% Na2CO3, dried over Na2SO4 and evaporated under vacuo to give 1.2 g of 2-bromo-5-dimethoxymethyl-pyridine as a brown oil.

Workup

  1. custompartitioned between water and Et2O
  2. extractionThe organic extract
  3. washwas washed with water, 5% Na2CO3
  4. dry with materialdried over Na2SO4
  5. customevaporated under vacuo

Sources & evidence

ORD record
ord-b5758aff07094646a32867b83bf4047b
Source dataset
uspto-grants-2011_11
Patent number
US08058273B2

Reaction notes

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