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Water → N-{[1-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-naphthyl]methyl}-aniline

HRID 634048
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 634048
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:9][C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]=1[B:20]1[O:24][C:23]([CH3:26])([CH3:25])[C:22]([CH3:28])([CH3:27])[O:21]1.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[CH3:25][C:23]1([CH3:26])[C:22]([CH3:27])([CH3:28])[O:21][B:20]([C:11]2[C:12]3[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:18]=[CH:19][C:10]=2[CH2:9][NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[O:24]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 962WaterHCID 6115AnilineHCID 11430Potassium CarbonateHCID 667958652-[2-(Bromomethyl)-1-naphthyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Produkt 1

HCID 131735478N-{[1-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-naphthyl]methyl}-aniline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 12.0 g (129 mmol) of aniline, 30.0 g (86.5 mmol) of 2-[2-(bromomethyl)-1-naphthyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, and 13.1 g (94.9 mmol) of K2CO3 in 500 cm3 of DMF was stirred for 12 h at 80° C. The resulting mixture was poured into 1000 cm3 of water. The product was extracted with 3×200 ml of ethyl acetate. The combined extract was dried over MgSO4 and then evaporated to dryness. An excess of aniline was distilled off using Kugelrohr apparatus. Yield 25.3 g (82%). Anal. calc. for C23H26BNO2: C, 76.89; H, 7.29; N, 3.90. Found: C, 77.02; H, 7.45; N, 3.70. 1H NMR (CDCl3): δ 8.19 (m, 1H, 8-H in naphthalene), 7.83 (d, J=8.8 Hz, 1H, 4-H in naphthalene), 7.80 (m, 1H, 5-H in naphthalene), 7.49 (d, J=8.8 Hz, 1H, 3-H in naphthalene), 7.40-7.51 (m, 2H, 6, 7-H in naphthalene), 7.19 (m, 2H, 2, 6-H in Ph), 6.75 (m, 1H, 4-H in Ph), 6.69 (m, 2H, 3, 5-H in Ph), 4.51 (s, 2H, CH2N), 4.07 (br.s, 1H, NH), 1.38 (s, 12H, Me in tetramethyldioxaborolane).

Aufarbeitung

  1. extractionThe product was extracted with 3×200 ml of ethyl acetate
  2. extractionThe combined extract
  3. dry with materialwas dried over MgSO4
  4. customevaporated to dryness
  5. distillationAn excess of aniline was distilled off

Quellen und Nachweise

ORD-Eintrag
ord-3c87b4ea52b946ac88681871d6ca689f
Quelldatensatz
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09321858B2

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