Phenylboronic Acid → 5-Methyl-2-phenylpyridine

HRID 1054102

Reaktionsgleichung

Reaktionsgleichung von HRID 1054102
Br[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][N:3]=1.[C:9]1(B(O)O)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>>[CH3:8][C:5]1[CH:6]=[CH:7][C:2]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[N:3][CH:4]=1

Komponenten

3

Edukt 2

HCID 66827Phenylboronic AcidHCID 5642162-Bromo-5-methylpyridine

Produkt 1

HCID 474675-Methyl-2-phenylpyridine

Versuchsvorschrift

Synthesized using 2-bromo-5-methyl-pyridine (2.92 g, 16.95 mmol) and phenylboronic acid (3.09 g, 25.4 mmol) according to Method C. Crude product was purified by flash chromatography on silica-gel using a mixture of hexane/ethyl acetate (8:1) as eluent. White solid. Yield: 1.99 g, 70%. 1H NMR (CDCl3, 500 MHz): δH (ppm)=2.38 (s, 3H), 7.37-7.43 (m, 1H), 7.44-7.51 (m, 2H), 7.54-7.60 (m, 1H), 7.60-7.67 (m, 1H), 7.95-8.00 (m, 2H), 8.51-8.55 (m, 1H); 13C NMR (CDCl3, 125 MHz): δC (ppm)=18.1, 120.0, 126.7, 128.6, 128.7, 131.5, 137.3, 139.4, 150.1, 154.8; (ESI): m/z=169.97 [M+H]+.

Aufarbeitung

  1. customSynthesized
  2. customCrude product was purified by flash chromatography on silica-gel
  3. additiona mixture of hexane/ethyl acetate (8:1) as eluent

Quellen und Nachweise

ORD-Eintrag
ord-e99bd8040e7b49ca8371bc54ffc45118
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09394290B2

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