p-Toluenesulfonic acid → 3-Bromo-4-(dimethoxymethyl)pyridine

HRID 80193Notes

Reaction equation

HRID 80193 reaction equation
[CH3:1]C1C=CC(S(O)(=O)=O)=CC=1.[Br:12][C:13]1[CH:14]=[N:15][CH:16]=[CH:17][C:18]=1[CH:19]=[O:20].[CH2:21]([O:23]C(=O)C)C>CO.CCCCCC>[Br:12][C:13]1[CH:14]=[N:15][CH:16]=[CH:17][C:18]=1[CH:19]([O:23][CH3:21])[O:20][CH3:1]

Participants

6

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 8857Ethyl AcetateHCID 27629973-Bromopyridine-4-carboxaldehyde

Product 1

HCID 207151453-Bromo-4-(dimethoxymethyl)pyridineYield 93.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8058HexaneSolvent

Procedure

PTSA (834 mg, 4.384 mmol) was added to a solution of 3-bromo-pyridine-4-carbaldehyde (600 mg, 3.2256 mmol) in methanol (20 mL). The resulting mixture was heated to reflux for 4 hours. The reaction was monitored by TLC (20% ethylacetate in hexane). The reaction mixture was concentrated and basified with NaHCO3 solution. The reaction mixture was partitioned between water and DCM. The organic layer was washed with brine solution, dried over Na7SO4, filtered and the filtrate was concentrated to afford 700 mg of 3-Bromo-4-dimethoxymethyl-pyridine (93.5% yield).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux for 4 hours
  3. concentrationThe reaction mixture was concentrated
  4. customThe reaction mixture was partitioned between water and DCM
  5. washThe organic layer was washed with brine solution
  6. dry with materialdried over Na7SO4
  7. filtrationfiltered
  8. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-01d6cc1ef2a0457f8f9467b2d8223657
Source dataset
uspto-grants-2014_09
Patent number
USRE045173E1

Reaction notes

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