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

HRID 2427505

반응식

HRID 2427505 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매2회

실험 절차

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)

후처리

  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

출처 및 근거

ORD 기록
ord-2e925621cf2a411b8ebcdf7d6157f0b4
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07968570B2

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