Sodium Carbonate → (4'-Fluorobiphenyl-2-yl)methanol

HRID 76856

Reaktionsgleichung

Reaktionsgleichung von HRID 76856
[F:1][C:2]1[CH:7]=[CH:6][C:5](B(O)O)=[CH:4][CH:3]=1.Br[C:12]1[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=1[CH2:14][OH:15].C([O-])([O-])=O.[Na+].[Na+]>COCCOC.CCOC(C)=O.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>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:12]2[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=2[CH2:14][OH:15])=[CH:4][CH:3]=1

Komponenten

8

Edukt 3

HCID 10340Sodium CarbonateHCID 728502-Bromobenzyl alcoholHCID 2856454-Fluorophenylboronic acid

Produkt 1

HCID 1392777(4'-Fluorobiphenyl-2-yl)methanol

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
115 °C

Versuchsvorschrift

To a mixture of 4-fluorophenylboronic acid (2.5 g, 13.4 mmol), 2-bromobenzyl alcohol (2.81 g, 20.1 mmol) and Pd(PPh3)4 (0.25 g, 0.216 mmol) in DME (20 mL) is added an aqueous solution of Na2CO3 (11.5 mL, 2.7 M, 31 mmol). The mixture is heated to 115° C. in sealed vessel overnight. The reaction is allowed to cool to room temperature and is diluted with EtOAc and water. The aqueous layer is extracted further with EtOAc (2×). The combined organic layers are washed with water, saturated NH4Cl, brine and dried over Na2SO4. After concentration, the resulting residue is purified by flash chromatography (hexane/CH2Cl2) to give (4′-fluorobiphenyl-2-yl)-methanol as oil. (cas #773871-75-3) 1H NMR (400 MHz, CDCl3) δ (ppm) 7.46-7.43 (m, 1H), 7.32-7.22 (m, 4H), 7.18-7.16 (m, 1H), 7.04-6.99 (m, 2H), 4.48 (d, J=5.5 Hz, 2H), 1.68 (br s, 1H).

Aufarbeitung

  1. temperatureto cool to room temperature
  2. extractionThe aqueous layer is extracted further with EtOAc (2×)
  3. washThe combined organic layers are washed with water, saturated NH4Cl, brine
  4. dry with materialdried over Na2SO4
  5. concentrationAfter concentration
  6. customthe resulting residue is purified by flash chromatography (hexane/CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-35d1dfceb3c64f939831b842566e1a97
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08835646B2

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