Potassium Carbonate → HCID 57969172, compound

HRID 1471517Notes

Reaction equation

HRID 1471517 reaction equation
Cl[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][N:3]=1.[Br:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][C:12]=1[CH2:18][OH:19].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Br:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][C:2]2[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][N:3]=2)=[CH:13][C:12]=1[CH2:18][OH:19]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27640536-Chloropyridine-3-carbaldehydeHCID 207854984-bromo-3-(hydroxymethyl)phenol

Product 1

HCID 57969172HCID 57969172, compoundYield 68.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Coupling reaction of 6-chloronicotinaldehyde (5.4 g, 38.15 mmol) and 4-bromo-3-(hydroxymethyl)phenol (8.15 g, 38.15 mmol) in the presence of K2CO3 (8.5 g, 1.5 eq) in DMF (100 mL) for 2 h at 100° C. under N2 gave the desired 6-(4-bromo-3-(hydroxymethyl)phenoxy)nicotinaldehyde (8.03 g, 26.1 mmol, yield 68.3%) as a white solid after silica gel column purification (hexane:EtOAc=3:1, v/v).

Sources & evidence

ORD record
ord-3dbf3deba15e40bf97cafda3d4771499
Source dataset
uspto-grants-2015_04
Patent number
US09012431B2

Reaction notes

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