Ethyl Acetate → HCID 71283746, compound

HRID 1752432Notes

Reaction equation

HRID 1752432 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.Br[C:10]1[CH:15]=[CH:14][C:13]([I:16])=[CH:12][N:11]=1.C([O-])([O-])=O.[Cs+].[Cs+].CCOC(C)=O>CN(C=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:10]2[CH:15]=[CH:14][C:13]([I:16])=[CH:12][N:11]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 97324-FluorophenolHCID 10796Cesium carbonateHCID 47382712-Bromo-5-iodopyridine

Product 1

HCID 71283746HCID 71283746, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 4-fluorophenol (1.12 g, 10 mmol), 2-bromo-5-iodopyridine (2.84 g, 10 mmol) and Cs2CO3 (3.83 g, 10 mmol) in DMF was stirred at 120° C. for 4 hrs. The reaction was worked up with EtOAc to give 2-(4-fluoro-phenoxy)-5-iodo-pyridine which was used for next step without further purification (crude yield 100%, yellowish solid). LC/MS: m/z=317 [M+H]+.

Sources & evidence

ORD record
ord-97b9ded4bf684e819de151b0c85898a9
Source dataset
uspto-grants-2015_10
Patent number
US09163008B2

Reaction notes

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