4-Fluorophenol → HCID 57782360, compound

HRID 1670850Notes

Reaction equation

HRID 1670850 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[C:9]([O-:12])([O-])=O.[Cs+].[Cs+].[CH3:15][N:16]1[C:21](=O)[N:20]([CH3:23])[CH2:19][CH2:18]C1.CO.[CH:26](Cl)(Cl)Cl>>[CH2:19]([N:20]1[C:23]([C:9](=[O:12])[CH3:26])=[CH:15][N:16]=[C:21]1[O:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)[CH3:18]

Participants

5

Reactant 4

HCID 97324-FluorophenolHCID 10796Cesium carbonateHCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-HCID 21584188Chloroform methanol

Product 1

HCID 57782360HCID 57782360, compound

Conditions

Temperature
200 °C

Procedure

A mixture of the compound obtained in Example 5-(2) (13.20 g), 4-fluorophenol (12.86 g), Cs2CO3 (49.9 g) and DMPU (15 ml) was stirred at 200° C. for 2 hours. After cooling to room temperature, MeOH/CHCl3 (MeOH/CHCl3=20%) was added and insoluble materials were filtered off. The filtrate was concentrated, and the resulting crude product was purified by column chromatography (OH-type neutral SiO2, AcOEt/hexane=0% to 30%) to give the titled compound (22.37 g, light-yellow oil).

Workup

  1. additionA mixture of the compound
  2. temperatureAfter cooling to room temperature
  3. filtrationinsoluble materials were filtered off
  4. concentrationThe filtrate was concentrated
  5. customthe resulting crude product was purified by column chromatography (OH-type neutral SiO2, AcOEt/hexane=0% to 30%)

Sources & evidence

ORD record
ord-e7a0e6f7b77b4b209ffaf9f121f5146d
Source dataset
uspto-grants-2011_08
Patent number
US07994204B2

Reaction notes

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