1,8-Diaminonaphthalene → 2-(3-Bromophenyl)-2,3-dihydro-1H-naphtho[1,8-de]-1,3,2-diazaborine

HRID 1846037

Reaktionsgleichung

Reaktionsgleichung von HRID 1846037
[Br:1][C:2]1[CH:3]=[C:4]([B:8](O)O)[CH:5]=[CH:6][CH:7]=1.[C:11]1([NH2:22])[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][C:19]=2[NH2:21])[CH:14]=[CH:13][CH:12]=1>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([B:8]2[NH:22][C:11]3[C:20]4[C:15]([CH:14]=[CH:13][CH:12]=3)=[CH:16][CH:17]=[CH:18][C:19]=4[NH:21]2)[CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 680671,8-DiaminonaphthaleneHCID 2734318(3-Bromophenyl)boronic acid

Produkt 1

HCID 533844122-(3-Bromophenyl)-2,3-dihydro-1H-naphtho[1,8-de]-1,3,2-diazaborineAusbeute 54 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A solution of 3-bromobenzene boronic acid (20 g, 0.1 mol) and naphthalene-1,8-diamine (17.3 g, 0.11 mol) in anhydrous toluene (600 mL) was heated to reflux for 16 hours. The reaction mixture was cooled to room temperature, then concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with petroleum ether:EtOAc 5:1 to afford the title compound as a grey solid in 54% yield, 23 g.

Aufarbeitung

  1. temperatureto reflux for 16 hours
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by silica gel column chromatography
  4. washeluting with petroleum ether:EtOAc 5:1

Quellen und Nachweise

ORD-Eintrag
ord-562e58f8917f4ef58c890f9fa3461faf
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08952008B2

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