Water → (6-Methyl-[1,1'-biphenyl]-3-yl)methanol

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Reaktionsgleichung

I[C:2]1[CH:3]=[C:4]([CH2:9][OH:10])[CH:5]=[CH:6][C:7]=1[CH3:8].[C:11]1(B(O)O)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(=O)([O-])[O-].[Na+].[Na+].O>C(O)CC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:8][C:7]1[C:2]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:3][C:4]([CH2:9][OH:10])=[CH:5][CH:6]=1

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

To a mixture of compound PPP, (3-iodo-4-methyl-phenyl)-methanol, (4 g, 16.12 mmol) and phenylboronic acid (2.06 g, 16.89 mmol) in 1-propanol (30 mL) was successively added palladium(II) acetate (0.01276 g, 0.05 mmol), triphenyl phosphine (0.042 g, 0.161 mmol), aq. sodium carbonate solution (2 M, 11.44 mL, 22.88 mmol), and water (6 mL). The mixture was heated to 100° C. until reaction is complete (tlc), cooled, quenched with water (20 mL) and extracted into ethyl acetate (3×50 mL). Combined organic layer was washed with 2% aq. sodium bicarbonate (2×25 mL), brine (1×50 mL), dried (MgSO4) and concentrated to yield 2.82 g of (6-methyl-biphenyl-3-yl)-methanol, compound QQQ, that was directly taken into next step without any further purification; Rt: 10.95 min.

Aufarbeitung

temperaturecooled
customquenched with water (20 mL)
extractionextracted into ethyl acetate (3×50 mL)
washCombined organic layer was washed with 2% aq. sodium bicarbonate (2×25 mL), brine (1×50 mL)
dry with materialdried (MgSO4)
concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag: ord-462e16135bfd4fd4924ff1c197cd328f
Quelldatensatz: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07981907B2

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