Sodium Carbonate → (2'-Chloro-3-methylbiphenyl-4-yl)methanol

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Reaktionsgleichung

Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][OH:9])=[C:4]([CH3:10])[CH:3]=1.[Cl:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1B(O)O.C([O-])([O-])=O.[Na+].[Na+]>C(O)CC.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Cl:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][OH:9])=[C:4]([CH3:10])[CH:3]=1

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

To a solution (4-bromo-2-methylphenyl)methanol (1 eq.) from Benzyl nitrile III.1 (Step 1) and 2-chlorophenylboronic acid (1.2 eq.) in n-propanol (0.1M) was added palladium acetate/triphenyl phosphine (1:3; 0.05 eq.) and aqueous Na2CO3 (2M; 3 eq.). The mixture was stirred at 80° C. for 2 h, cooled to room temperature, poured in water and extracted with EtOAc. The organic extract was washed with, brine, dried over MgSO4 filtered and concentrated. Purification by column chromatography on silica gel (Combi-Flash by ISCO), eluting with Hex/EtOAc (0 to 75% in 30 min) to afforded the desired compound.

Aufarbeitung

temperaturecooled to room temperature
extractionextracted with EtOAc
extractionThe organic extract
washwas washed with, brine
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated
customPurification by column chromatography on silica gel (Combi-Flash by ISCO)
washeluting with Hex/EtOAc (0 to 75% in 30 min)

Quellen und Nachweise

ORD-Eintrag: ord-d9bba7d36a6d4d7093e4d41c531001d7
Quelldatensatz: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08334308B2

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