Boron tribromide → HCID 87364811, Verbindung

HRID 1850095Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1850095
[F:1][C:2]([F:19])([F:18])[C:3]([N:5]1[CH2:9][CH2:8][CH:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[O:16]C)[CH2:6]1)=[O:4].B(Br)(Br)Br.C([O-])(O)=O.[Na+]>C(Cl)Cl>[F:19][C:2]([F:1])([F:18])[C:3]([N:5]1[CH2:9][CH2:8][CH:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[OH:16])[CH2:6]1)=[O:4]

Komponenten

5

Edukt 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 584046022,2,2-Trifluoro-1-[3-(2-methoxyphenyl)pyrrolidin-1-yl]ethan-1-one

Produkt 1

HCID 87364811HCID 87364811, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To the title compound of Example 43 Step A (1.2 g, 4.4 mmol) in CH2Cl2 (15 mL) at 0° C. was added BBr3 (1M in CH2Cl2, 9.8 mL, 9.8 mmol). After warming to rt and allowing to stir for 18 h, sat'd NaHCO3 (aq.) was added slowly. The reaction was then extracted with CH2Cl2. The combined organic layers were dried and used in the next step without further purification. MS (ESI): mass calcd. for C12H12F3NO2, 259.2. m/z found, 260.1 [M+H]+. 1H NMR (CDCl3): 7.22-7.11 (m, 2H), 6.97-6.88 (m, 1H), 6.87-6.77 (m, 1H), 4.26-4.14 (m, 1H), 4.04-3.94 (m, 0.5H), 3.93-3.84 (m, 0.5H), 3.82-3.71 (m, 1H), 3.70-3.53 (m, 2H), 2.44-2.26 (m, 1.5H), 2.25-2.13 (m, 0.5H).

Aufarbeitung

  1. extractionThe reaction was then extracted with CH2Cl2
  2. customThe combined organic layers were dried
  3. customused in the next step without further purification

Quellen und Nachweise

ORD-Eintrag
ord-28987f04bb78457e9d969d103fffe296
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08957059B2

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