2-Bromo-4'-methylacetophenone → 2-((3-Bromobenzyl)(methyl)amino)-1-p-tolylethanone

HRID 576091

반응식

HRID 576091 반응식
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[CH2:5][NH:6][CH3:7].C(N(C(C)C)CC)(C)C.Br[CH2:21][C:22]([C:24]1[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=1)=[O:23]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[CH2:5][N:6]([CH3:7])[CH2:21][C:22]([C:24]1[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=1)=[O:23]

참가 물질

5

반응물 3

HCID 692722-Bromo-4'-methylacetophenoneHCID 81531DiisopropylethylamineHCID 457588Benzenemethanamine, 3-bromo-N-methyl-

생성물 1

HCID 620376912-((3-Bromobenzyl)(methyl)amino)-1-p-tolylethanone수율 98.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

To a solution of (3-bromo-benzyl)-methyl-amine (3.0 g, 15.0 mmol) in methylene chloride (60 mL) was added diisopropylethylamine (5.2 mL, 30.0 mmol). The reaction mixture was cooled to 0° C. and treated with 2-bromo-1-p-tolyl-ethanone (3.19 g, 15.0 mmol) portionwise over a period of 10 minutes. The reaction mixture was warmed to room temperature and stirred for 4 hours. The reaction mixture was washed with water (3×), dried over sodium sulfate, filtered, and the solvent was evaporated to afford 2-((3-bromobenzyl)(methyl)amino)-1-p-tolylethanone (4.89 g, 98%) as a viscous, orange oil: 1H NMR (CDCl3, 500 MHz) δ 7.85 (d, J=8.2 Hz, 2H), 7.51 (br s, 1H), 7.38 (d, J=7.9 Hz, 1H), 7.28-7.23 (m, 3H), 7.17 (t, J=7.8 Hz, 1H), 3.78 (s, 2H), 3.63 (s, 2H), 2.41 (s, 3H), 2.35 (s, 3H).

후처리

  1. temperatureThe reaction mixture was warmed to room temperature
  2. washThe reaction mixture was washed with water (3×)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customthe solvent was evaporated

출처 및 근거

ORD 기록
ord-5086e6e3f24a40769062a1c9b38f7a48
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09034899B2

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