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

HRID 2427505

反応式

HRID 2427505 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒2 回

実験手順

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)

後処理

  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

出典と根拠

ORDレコード
ord-2e925621cf2a411b8ebcdf7d6157f0b4
出典データセット
uspto-grants-2011_06
特許番号
US07968570B2

関連ノート

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