(6-Bromo-5-methoxypyridin-2-yl)methanol → 6-Bromo-5-methoxypicolinaldehyde

HRID 1519427Notes

Reaction equation

HRID 1519427 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([CH2:8][OH:9])[CH:5]=[CH:4][C:3]=1[O:10][CH3:11]>ClCCl.O=[Mn]=O>[Br:1][C:2]1[N:7]=[C:6]([CH:8]=[O:9])[CH:5]=[CH:4][C:3]=1[O:10][CH3:11]

Participants

4

Reactant 1

HCID 16044667(6-Bromo-5-methoxypyridin-2-yl)methanol

Product 1

HCID 222683396-Bromo-5-methoxypicolinaldehydeYield 63%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of (6-bromo-5-methoxypyridin-2-yl)methanol (2.30 g, 10 mmol) in dichloromethane (50 mL) was added MnO2 (8.0 g) at rt. The reaction mixture was stirred at rt for 24 h. After that time the reaction was cooled to rt, filtered to remove solids and concentrated under reduced pressure to give 6-bromo-5-methoxypicolinaldehyde (1.35 g, 63%) as an off-white solid: 1H NMR (400 MHz, CDCl3): δ 9.94 (s, 1H), 7.96 (d, J=8.4 Hz, 1H), 7.27 (d, J=8.0 Hz, 1H), 4.03 (s, 3H).

Workup

  1. temperatureAfter that time the reaction was cooled to rt
  2. filtrationfiltered
  3. customto remove solids
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7df99774a99e427a81f76a690dde90af
Source dataset
uspto-grants-2015_07
Patent number
US09073878B2

Reaction notes

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