Potassium Carbonate → 4'-(Trifluoromethyl)[1,1'-biphenyl]-3-ol

HRID 1157424Notes

Reaction equation

HRID 1157424 reaction equation
I[C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[F:9][C:10]([F:21])([F:20])[C:11]1[CH:16]=[CH:15][C:14](B(O)O)=[CH:13][CH:12]=1.C([O-])([O-])=O.[K+].[K+]>O.[Pd]>[F:9][C:10]([F:21])([F:20])[C:11]1[CH:16]=[CH:15][C:14]([C:2]2[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=2)=[CH:13][CH:12]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 122723-IodophenolHCID 27343894-(Trifluoromethyl)phenylboronic acid

Product 1

HCID 220549964'-(Trifluoromethyl)[1,1'-biphenyl]-3-ol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Conditions

Temperature
170 °C

Procedure

To a mixture of 10% Pd/C (cat), 3-iodophenol (220 mg, 1.00 mmol) and 4-(trifluoromethyl)phenylboronic acid (284 mg, 1.49 mmol) was added a solution of K2CO3 (415 mg, 3.01 mmol) in water (10 mL) and the reaction mixture was heated in a Biotage microwave (170° C., absorption high, pre-stirring 10 s) for 20 min. The crude reaction mixture was then extracted into EtOAc (40 mL×3) and dried over MgSO4 to yield 3-(4-(trifluoromethyl)phenyl)phenol as a yellow solid (212 mg, 89%, 99% purity by HPLC) which was used without further purification.

Workup

  1. customThe crude reaction mixture
  2. extractionwas then extracted into EtOAc (40 mL×3)
  3. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-387c16d324b3437cbf23cbc0b104175c
Source dataset
uspto-grants-2010_10
Patent number
US07807685B2

Reaction notes

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