Hexane → Diphenyl-(4-(4,4,5,5-tetramethyl-(1,3,2)dioxaborolan-2-yl)-phenyl)-amine

HRID 1261872

Reaktionsgleichung

Reaktionsgleichung von HRID 1261872
[CH:1]1[CH:6]=[CH:5][C:4]([N:7]([C:14]2[CH:19]=[CH:18][C:17](Br)=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:3][CH:2]=1.[Li]CCCC.CCCCCC.C(O[B:36]1[O:40][C:39]([CH3:42])([CH3:41])[C:38]([CH3:44])([CH3:43])[O:37]1)(C)C>O.C1(C)C=CC=CC=1.C1COCC1>[C:4]1([N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:14]2[CH:19]=[CH:18][C:17]([B:36]3[O:40][C:39]([CH3:42])([CH3:41])[C:38]([CH3:44])([CH3:43])[O:37]3)=[CH:16][CH:15]=2)[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=1

Komponenten

8

Edukt 4

HCID 8058HexaneHCID 6428384-BromotriphenylamineHCID 50177412-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 178418339Butyllithium

Produkt 1

HCID 11639307Diphenyl-(4-(4,4,5,5-tetramethyl-(1,3,2)dioxaborolan-2-yl)-phenyl)-amineAusbeute 45 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To a flame-dried 3-neck, round-bottomed 500 mL flask equipped with mechanical stirring and an addition funnel was added 4-bromotriphenylamine (12.5 g, 39.5 mmol) and THF (250 mL) by cannula. The solution was cooled to −78° C. and 1.6 M n-BuLi in hexane (26.5 mL, 42.4 mmol) was added by addition funnel over 15 min. After stirring for 30 min, 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (9.8 mL, 48.2 mmol) was added dropwise, and the reaction mixture was allowed to warm to room temperature overnight. Toluene and water were added, and the organic phase was further washed with water, dried with MgSO4, and concentrated. The crude product was purified by column chromatography eluting with hexane, 2/1 hexane/CH2Cl2, and finally 1/1 hexane/CH2Cl2 to give 6.4 g (45%) white crystals. 1H NMR (400 MHz, CDCl3) δ: 7.66 (m, 2H), 7.26 (m, 4H), 7.10 (m, 4H), 7.04 (m, 4H); GC-MS (m/z): 371 (M+), >97% purity. Anal. Calcd. for C24H26BNO2: C, 77.64%; H, 7.06%; B, 2.91%; N, 3.77%. Found: C, 77.78%; H, 7.21%; B, 2.70%; N, 3.53%.

Aufarbeitung

  1. customTo a flame-dried 3-neck, round-bottomed 500 mL flask equipped
  2. stirringAfter stirring for 30 min
  3. temperatureto warm to room temperature overnight
  4. washthe organic phase was further washed with water
  5. dry with materialdried with MgSO4
  6. concentrationconcentrated
  7. customThe crude product was purified by column chromatography
  8. washeluting with hexane, 2/1 hexane/CH2Cl2, and finally 1/1 hexane/CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-a48ce86daca946aebe88677c8e339b5f
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08471035B1

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