Trimethyl orthoformate → 5-Bromo-2-chloro-3-dimethoxymethyl-pyridine

HRID 1629741Notes

Reaction equation

HRID 1629741 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5]([Cl:10])=[C:6]([CH:9]=1)C=O.[CH3:11][O:12][CH:13](OC)[O:14][CH3:15].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO.C(Cl)Cl>[Br:1][C:2]1[CH:9]=[C:6]([CH:13]([O:14][CH3:15])[O:12][CH3:11])[C:5]([Cl:10])=[N:4][CH:3]=1

Participants

6

Reactant 3

HCID 9005Trimethyl orthoformateHCID 521998p-Toluenesulfonic acid monohydrateHCID 230909885-Bromo-2-chloropyridine-3-carbaldehyde

Product 1

HCID 242292075-Bromo-2-chloro-3-dimethoxymethyl-pyridine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 5-bromo-2-chloronicotinaldehyde (981 mg, 2.43 mmol), trimethylorthoformate (1.46 mL, 13.4 mmol) and p-toluenesulfonic acid monohydrate (42.3 mg, 0.222 mmol) in MeOH (18 mL) was refluxed for 16 hours. The mixture was diluted in CH2Cl2 and washed with 10% aqueous potassium carbonate and brine, dried over sodium sulfate, filtered and concentrated. The crude product was used in the next step without further purification.

Workup

  1. temperaturewas refluxed for 16 hours
  2. washwashed with 10% aqueous potassium carbonate and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was used in the next step without further purification

Sources & evidence

ORD record
ord-b20b1db65a024ed6b64785a01aca9a97
Source dataset
uspto-grants-2014_07
Patent number
US08791100B2

Reaction notes

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