Hydrochloric Acid → HCID 57588589, compound

HRID 1782679Notes

Reaction equation

HRID 1782679 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2[C:13]3[O:14][C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=4[C:12]=3[CH:11]=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.[OH:21][C:22]1[CH:27]=[CH:26][C:25](B(O)O)=[CH:24][CH:23]=1.C([O-])([O-])=O.[Na+].[Na+].Cl>C1(C)C=CC=CC=1.C(O)C.O.C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:11]1[C:12]2[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[O:14][C:13]=2[C:8]([C:4]2[CH:3]=[C:2]([C:25]3[CH:26]=[CH:27][C:22]([OH:21])=[CH:23][CH:24]=3)[CH:7]=[CH:6][CH:5]=2)=[CH:9][CH:10]=1

Participants

10

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 27343604-Hydroxyphenylboronic acidHCID 59855508HCID 59855508, compound

Product 1

HCID 57588589HCID 57588589, compound

Reagents, catalysts & solvents 5

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 4-(3-bromo-phenyl)-dibenzofuran (0.62 mmol), 4-hydroxyphenyl boronic acid (0.62 mmol), and Pd(PPh3)4, (0.05 mmol) in 2 mL of toluene and 1 mL ethanol was heated to obtain a clear solution, then Na2CO3 (1.9 mmol) in 2 mL water was added. The reaction mixture refluxed for 5 h at 80° C. The mixture was cooled to room temperature and the aqueous layer was acidified with 2N HCl. The entire reaction mixture was diluted with 25 mL ethyl acetate. The organic layer was washed with 2×30 mL portions of water, 2×30 mL portions of sat. aq. NaCl, and dried (MgSO4). After the solution was concentrated, the residue was purified by column chromatography (eluted with 5-10% EtOAc-Heptane) to afford 3′-Dibenzofuran-4-yl-biphenyl-4-ol.

Workup

  1. temperaturewas heated
  2. customto obtain a clear solution
  3. temperatureThe mixture was cooled to room temperature
  4. customThe entire reaction mixture
  5. washThe organic layer was washed with 2×30 mL portions of water, 2×30 mL portions of sat. aq. NaCl
  6. dry with materialdried (MgSO4)
  7. concentrationAfter the solution was concentrated
  8. customthe residue was purified by column chromatography (eluted with 5-10% EtOAc-Heptane)

Sources & evidence

ORD record
ord-601a9a85a17547e6be9054fa64ff6c66
Source dataset
uspto-grants-2009_03
Patent number
US07498356B2

Reaction notes

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