Water → 5-(2-Bromovinyl)-2-methylpyridine

HRID 2176087Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2176087
[CH3:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/B2OC(C)(C)C(C)(C)O2)=[CH:4][N:3]=1.[Br:19]N1C(=O)CCC1=O.C(N(CC)CC)C.O>C(#N)C>[Br:19][CH:9]=[CH:8][C:5]1[CH:6]=[CH:7][C:2]([CH3:1])=[N:3][CH:4]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 67184N-bromobutanimideHCID 57416208(e)-2-Methyl-5-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)vinyl)pyridine

Produkt 1

HCID 722566695-(2-Bromovinyl)-2-methylpyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A solution of (E)-2-methyl-5-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)vinyl)-pyridine (1.0 g, 4.08 mmol; Example 23B) in acetonitrile (10 mL) was treated with N-bromosuccinimide (0.346 mL, 4.08 mmol; Aldrich) and triethylamine (0.625 mL, 4.49 mmol; Aldrich) and stirred at room temperature for 16 hours. Water was added and the mixture was extracted several times with ethyl acetate. The combined organic extracts were concentrated, and the resulting material was purified by flash chromatography (silica gel, hexane/ethyl acetate, 3:1) to afford the title compound as a 1.2:1 Z/E mixture: 1H NMR (300 MHz, CDCl3) δ ppm 2.54 (s, 3H), 2.57 (s, 3.6H), 6.52 (d, J=14 Hz, 1.2H), 6.75-6.85 (d, J=14 Hz, 1H), 7.01-7.22 (m, 4.4H), 7.52 (dd, J=8, 2 Hz, 1H), 8.07 (dd, J=8, 2 Hz, 1.2H), 8.43 (d, J=2 Hz, 1H), 8.66 (d, J=2 Hz, 1.2H); MS (DCI/NH3) m/z 198/200 (M+H)+.

Aufarbeitung

  1. extractionthe mixture was extracted several times with ethyl acetate
  2. concentrationThe combined organic extracts were concentrated
  3. customthe resulting material was purified by flash chromatography (silica gel, hexane/ethyl acetate, 3:1)

Quellen und Nachweise

ORD-Eintrag
ord-364b3651b86448148781e30cfb4b8f42
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09063126B2

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