Methyl morpholine oxide → 4-Bromo-6-chloropyridine-3-carbaldehyde

HRID 879527Notes

Reaction equation

HRID 879527 reaction equation
[Br:1][C:2]1[C:7]([CH2:8]Br)=[CH:6][N:5]=[C:4]([Cl:10])[CH:3]=1.C[N+]1([O-])CC[O:15]CC1>C(#N)C.CCOC(C)=O>[Br:1][C:2]1[C:7]([CH:8]=[O:15])=[CH:6][N:5]=[C:4]([Cl:10])[CH:3]=1

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 867003464-Bromo-5-(bromomethyl)-2-chloropyridine

Product 1

HCID 665107774-Bromo-6-chloropyridine-3-carbaldehyde

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

A flask was charged with 4-bromo-5-(bromomethyl)-2-chloropyridine (490 mg, 1.72 mmol), powdered 4 Å molecular sieves, and NMO (2.19 g, 18.74 mmol) then diluted with ACN (17 mL) and stirred at room temperature for 1 h. The reaction mixture was diluted with EtOAc, filtered, and concentrated in vacuo. The crude residue was purified by silica gel column chromatography (0-20% EtOAc/Hex gradient) to afford the desired product. LCMS-ESI+: calc'd for C6H4BrClNO 219.9 (M+H+); Found: 220.0 (M+H+).

Workup

  1. filtrationfiltered
  2. concentrationconcentrated in vacuo
  3. customThe crude residue was purified by silica gel column chromatography (0-20% EtOAc/Hex gradient)

Sources & evidence

ORD record
ord-1d35b466a0b04c46a5f7a704dd95f759
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

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