4-Iodophenol → 4-Fluoro-4'-hydroxybiphenyl

HRID 459229Notes

Reaction equation

HRID 459229 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[F:9][C:10]1[CH:15]=[CH:14][C:13](B(O)O)=[CH:12][CH:11]=1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.O.CC([O-])=O.CC([O-])=O.[Pd+2]>[F:9][C:10]1[CH:15]=[CH:14][C:13]([C:2]2[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=2)=[CH:12][CH:11]=1

Participants

6

Reactant 3

HCID 108944-IodophenolHCID 11430Potassium CarbonateHCID 2856454-Fluorophenylboronic acid

Product 1

HCID 3454204-Fluoro-4'-hydroxybiphenyl

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 218864351,4-Dioxane--water (1/1)Solvent

Conditions

Temperature
100 °C

Procedure

A mixture of p-Iodophenol linked to the Wang's resin from Step A (1 eq), 4-fluorobenzene boronic acid (6 eq), K2CO3 (12 eq) and Pd(OAc)2 (0.5 eq) were suspended in a mixture of dioxane/water (6/1) and the mixture was heated at 100° C. and stirring for 36 hours. The resin was washed with DMF/H2O and MeOH/THF/HCl diluted and MeOH/CH2Cl2. After it was dried, was suspended in dichloromethane, and TFA 95% was added. The mixture was stirred at room temperature for 30 min then filtered and washed with MeOH and dichloromethane. The solvents were concentrated to dryness to give the title product.

Workup

  1. washThe resin was washed with DMF/H2O and MeOH/THF/HCl
  2. additiondiluted
  3. customAfter it was dried
  4. additionTFA 95% was added
  5. stirringThe mixture was stirred at room temperature for 30 min
  6. filtrationthen filtered
  7. washwashed with MeOH and dichloromethane
  8. concentrationThe solvents were concentrated to dryness

Sources & evidence

ORD record
ord-56432046585c4863b8fb0f25ea7946b0
Source dataset
uspto-grants-2007_03
Patent number
US07192982B2

Reaction notes

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