Sodium Carbonate → Biphenyl

HRID 893043Notes

Reaction equation

HRID 893043 reaction equation
CO[C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.CO.O.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>[C:3]1([C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

7

Reactant 2

HCID 10340Sodium CarbonateHCID 201262(4-Methoxyphenyl)boronic acid

Product 1

HCID 7095BiphenylYield 107.1%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 887MethanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

In 10 ml of toluene was added 600 mg (1.11 mmoles) of (4-bromophenyl)perfluorohexyl sulfone, and 20 mg (0.17 mmoles) of Pd(PPh3)4. To this clear colorless solution was added 170 mg (1.12 mmoles) of 4-methoxyphenylboronic acid in 2 ml of methanol, 240 mg (2.26 mmoles) of Na2CO3 in 1 ml of water. The mixture was stirred under nitrogen at 80° C. overnight. Isolation in accordance with the procedure of Example 9 gave after flash chromatography (silica gel, 50% CHCl3 /hexane) 343 mg of the biphenyl (0.60 mmoles, 54.6%). Elemental analyses: Found: C: 40.29; H: 2.03; calculated for C19H11F13O3S: C: 40.30; H: 1.96 Mp: 101.5°-103° C. SHG: not active. 1H nmr (CD2Cl2): 8.05 (d, J=8.6 Hz, 2H), 7.87 (d, J=8.6Hz, 2H), 7.65 (d, J=8.8 Hz, 2H), 7.04 (d, J=8.8 Hz, 2H), 3.87 (s 3H).

Sources & evidence

ORD record
ord-bccc4386ae2f4c5aa885c465a8a58d93
Source dataset
uspto-grants-1992_06
Patent number
US05120876

Reaction notes

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