(2-Bromo-4-methylthiazol-5-yl)methanol → 2-bromo-4-methylthiazole-5-carbaldehyde

HRID 1406302Notes

Reaction equation

HRID 1406302 reaction equation
[Br:1][C:2]1[S:3][C:4]([CH2:8][OH:9])=[C:5]([CH3:7])[N:6]=1>C(Cl)(Cl)Cl.O=[Mn]=O>[Br:1][C:2]1[S:3][C:4]([CH:8]=[O:9])=[C:5]([CH3:7])[N:6]=1

Participants

4

Reactant 1

HCID 59295463(2-Bromo-4-methylthiazol-5-yl)methanol

Product 1

HCID 771748872-bromo-4-methylthiazole-5-carbaldehydeYield 47%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6212ChloroformSolvent

Procedure

A mixture of (2-bromo-4-methylthiazol-5-yl)methanol of preparation 97 (3.8 g, 18.4 mmol) and MnO2 (16.5 g, 0.18 mmol) in CHCl3 (180 mL) was stirred at room temperature overnight. TLC (petroleum ether/EtOAc=3:1) showed the reaction was complete. The reaction mixture was filtered and the filtrate was concentrated in vacuum. The residue was purified by a Biotage silica gel cartridge (EA/PE=30%, Rf=0.5) to give the title compound as a white solid (1.8 g, 47%) as a white solid, and as well as impure 2-bromo-4-methylthiazole-5-carbaldehyde (1.3 g, 34%) as an off-white solid.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated in vacuum
  3. customThe residue was purified by a Biotage silica gel cartridge (EA/PE=30%, Rf=0.5)

Sources & evidence

ORD record
ord-a65df0c0dffe41ff9de7d8a993b7d831
Source dataset
uspto-grants-2014_12
Patent number
US08916593B2

Reaction notes

Loading…