Hydrogen Bromide → 5-Bromomethyl-7-methyl-2-(4-trifluoromethoxybenzyl)-2,3-dihydroisoindol-1-one

HRID 2427505

Reaktionsgleichung

Reaktionsgleichung von HRID 2427505
N[CH2:2][C:3]1[CH:4]=[C:5]2[C:9](=[C:10]([CH3:12])[CH:11]=1)[C:8](=[O:13])[N:7]([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][C:22]([F:25])([F:24])[F:23])=[CH:17][CH:16]=1)[CH2:6]2.[N+]([O-])([O-])=O.[Na+].[BrH:31]>O>[Br:31][CH2:2][C:3]1[CH:4]=[C:5]2[C:9](=[C:10]([CH3:12])[CH:11]=1)[C:8](=[O:13])[N:7]([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][C:22]([F:25])([F:24])[F:23])=[CH:17][CH:16]=1)[CH2:6]2

Komponenten

5

Edukt 3

HCID 260Hydrogen BromideHCID 24268Sodium NitrateHCID 579493205-Aminomethyl-7-methyl-2-(4-trifluoromethoxybenzyl)-2,3-dihydroisoindol-1-one

Produkt 1

HCID 579495755-Bromomethyl-7-methyl-2-(4-trifluoromethoxybenzyl)-2,3-dihydroisoindol-1-oneAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Versuchsvorschrift

5-Aminomethyl-7-methyl-2-(4-trifluoromethoxybenzyl)-2,3-dihydroisoindol-1-one (0.5 g, 1.43 mmol) was dissolved in a solution of water (10 mL) and 48% HBr (1 mL). The solution was chilled in an ice bath. A solution of sodium nitrate (0.17 g, 2.4 mmol) in water (5 mL) was added dropwise. A white solid formed. The reaction was allowed to stand for 30 minutes, and then the water was decanted off. The solid was chromatographed on silica gel, eluting with methylene chloride, to give 0.42 g (70% yield) of the title compound as a white solid. 1H NMR (300.132 MHz, CDCl3) δ 7.23-7.15 (m, 4H), 7.35-7.30 (m, 2H), 4.76 (s, 2H), 4.48 (s, 2H), 4.22 (s, 2H), 2.75 (s, 3H)

Aufarbeitung

  1. temperatureThe solution was chilled in an ice bath
  2. customA white solid formed
  3. customthe water was decanted off
  4. customThe solid was chromatographed on silica gel
  5. washeluting with methylene chloride

Quellen und Nachweise

ORD-Eintrag
ord-2e925621cf2a411b8ebcdf7d6157f0b4
Quelldatensatz
uspto-grants-2011_06
Patentnummer
US07968570B2

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