Sodium Hydroxide → 3-Bromo-2-ethynyl-5-(trifluoromethyl)benzenamine

HRID 913898Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 913898
[OH-].[Na+].[Br:3][C:4]1[C:5]([C:15]#[C:16][Si](C)(C)C)=[C:6]([CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1)[NH2:7]>CO>[Br:3][C:4]1[C:5]([C:15]#[CH:16])=[C:6]([CH:8]=[C:9]([C:11]([F:12])([F:13])[F:14])[CH:10]=1)[NH2:7]

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 575462013-Bromo-5-(trifluoromethyl)-2-[(trimethylsilyl)ethynyl]aniline

Produkt 1

HCID 575460303-Bromo-2-ethynyl-5-(trifluoromethyl)benzenamine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Sodium hydroxide (3.17 mL, 31.7 mmol) was added to a solution of 3-bromo-5-(trifluoromethyl)-2-((trimethylsilyl)ethynyl)aniline (10.67 g, 31.7 mmol) in methanol (200 mL) and was stirred for 30 min. The solvent was evaporated. The residue was taken up in brine (30 mL) and extracted with ethyl acetate (3×100 mL). The combined organic layers were dried with magnesium sulfate and evaporated. The residue was purified on silica gel with 10% ethyl acetate/hexanes to give 7.54 g (90%) as a tan solid. 1H-NMR (CDCl3, 400 MHz) δ 7.15 (s, 1H), 6.85 (s, 1H), 4.58 (bs, 2H), 3.77 (s, 1H); LC/MS (HPLC method 4): tR=3.186 min, 263.89(MH)+.

Aufarbeitung

  1. customThe solvent was evaporated
  2. extractionextracted with ethyl acetate (3×100 mL)
  3. dry with materialThe combined organic layers were dried with magnesium sulfate
  4. customevaporated
  5. customThe residue was purified on silica gel with 10% ethyl acetate/hexanes
  6. customto give 7.54 g (90%) as a tan solid

Quellen und Nachweise

ORD-Eintrag
ord-66841eac2b50461c98040adce21fa3c7
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08026257B2

Notizen zur Reaktion

Wird geladen…