Phenol → HCID 67125487, compound

HRID 1430271Notes

Reaction equation

HRID 1430271 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].F[C:11]1[CH:16]=[C:15]([I:17])[CH:14]=[CH:13][N:12]=1>CN(C)C=O.C(OCC)(=O)C>[I:17][C:15]1[CH:14]=[CH:13][N:12]=[C:11]([O:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:16]=1

Participants

6

Reactant 3

HCID 996PhenolHCID 24758Sodium hydrideHCID 70235702-Fluoro-4-iodopyridine

Product 1

HCID 67125487HCID 67125487, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

Phenol (0.464 g) in N,N-dimethylformamide (5 mL) was treated with sodium hydride (60% in mineral oil, 0.057 g). After the gas evolution ceased, 2-fluoro-4-iodopyridine (0.22 g) was added slowly to the solution. The mixture was heated at 100° C. overnight under nitrogen atmosphere, cooled, diluted with ethyl acetate and washed with aqueous NaOH. The organic layer was concentrated and purified by preparative TLC, eluting with petroleum ether/ethyl acetate (10/1).

Workup

  1. temperaturecooled
  2. washwashed with aqueous NaOH
  3. concentrationThe organic layer was concentrated
  4. custompurified by preparative TLC
  5. washeluting with petroleum ether/ethyl acetate (10/1)

Sources & evidence

ORD record
ord-499ff39362624a10be688defe18f16f4
Source dataset
uspto-grants-2015_01
Patent number
US08940737B2

Reaction notes

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