(5-Bromo-3-pyridinyl)methanol → HCID 11702341, compound

HRID 551591Notes

Reaction equation

HRID 551591 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:8]=O)[CH:5]=[N:6][CH:7]=1.Br[C:11]1[CH:12]=[C:13](CO)[CH:14]=[N:15][CH:16]=1>C(Cl)(Cl)Cl.O=[Mn]=O>[N:15]1([CH2:4][CH2:3][C:2]#[C:7][C:2]2[CH:7]=[N:6][CH:5]=[C:4]([CH2:8][N:15]3[CH2:16][CH2:11][CH2:12][CH2:13][CH2:14]3)[CH:3]=2)[CH2:16][CH2:11][CH2:12][CH2:13][CH2:14]1

Participants

5

Reactant 2

HCID 2784733(5-Bromo-3-pyridinyl)methanolHCID 27847345-Bromo-3-pyridinecarboxaldehyde

Product 1

HCID 11702341HCID 11702341, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6212ChloroformSolvent

Procedure

5-Bromo-pyridine-3-carbaldehyde. (5-Bromo-pyridin-3-yl)-methanol (1.13 g, 6.00 mmol) was dissolved in CHCl3 (40 mL) and treated with MnO2 (3.60 g). The reaction mixture was heated at reflux temperature for 3 h. The hot reaction mixture was filtered through a pad of diatomaceous earth and the filtrate was concentrated to yield the title compound (0.570 g, 51%).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux temperature for 3 h
  3. filtrationThe hot reaction mixture was filtered through a pad of diatomaceous earth
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-70b56f8b33e542269ef8932d9dac3164
Source dataset
uspto-grants-2011_05
Patent number
US07947718B2

Reaction notes

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