Pyridine → HCID 67442762, compound

HRID 1666778Notes

Reaction equation

HRID 1666778 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:11]=[C:12]([CH:16]2[O:20][CH2:19][CH2:18][O:17]2)[CH:13]=[CH:14][CH:15]=1.C(=O)([O-])[O-].[K+].[K+].N1C=CC=CC=1>ClCCl.[Cu]=O.CCOC(C)=O.CCCCCC>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:14]2[CH:13]=[C:12]([CH:16]3[O:17][CH2:18][CH2:19][O:20]3)[CH:11]=[CH:10][CH:15]=2)=[CH:4][CH:3]=1

Participants

9

Reactant 4

HCID 1049PyridineHCID 97324-FluorophenolHCID 11430Potassium CarbonateHCID 873062-(3-Bromophenyl)-1,3-dioxolane

Product 1

HCID 67442762HCID 67442762, compound

Reagents, catalysts & solvents 4

HCID 14829Copper oxideCatalystHCID 6344DichloromethaneSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

Combine 4-fluorophenol (3.0 g, 227.8 mmol), 2-(3-bromophenyl)-1,3-dioxolane (5.0 ml, 33.3 mmol), potassium carbonate (anhydrous, 8.0 g, 55.6 mmol), and dry pyridine (50 ml). Heat to 90° C. and add copper oxide (5.5 g, 69.5 mmol). Heat at reflux. After 24 hours, cool to room temperature, dilute with dichloromethane, and filter. Concentrate the filtrate in vacuum to give a yellow oil. Chromatograph the oil on silica gel eluting with 95:5 hexane:EtOAc to give the title compound.

Workup

  1. temperatureHeat
  2. temperatureat reflux
  3. temperaturecool to room temperature
  4. filtrationfilter
  5. concentrationConcentrate the filtrate in vacuum
  6. customto give a yellow oil

Sources & evidence

ORD record
ord-c5b9c3ddb55c4de8887f9ed78d10d573
Source dataset
uspto-grants-2011_10
Patent number
US08044090B2

Reaction notes

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