P-Anisidine → 2-Bromo-4-methoxyaniline

HRID 1003255노트

반응식

HRID 1003255 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][CH:4]=1.C(=O)([O-])[O-].[Na+].[Na+].[Br:16]Br.C(OCC)(=O)C>ClCCl.CCCCCC>[Br:16][C:7]1[CH:8]=[C:3]([O:2][CH3:1])[CH:4]=[CH:5][C:6]=1[NH2:9]

참가 물질

7

반응물 4

HCID 7732P-AnisidineHCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 24408Bromine

생성물 1

HCID 108996712-Bromo-4-methoxyaniline수율 25%

시약·촉매·용매 2

HCID 6344Dichloromethane용매3회HCID 8058Hexane용매

실험 절차

To a solution of p-anisidine (10 g, 0.08 mol) and sodium carbonate (17.2 g, 0.16 mol) in dichloromethane (400 ml) was added a solution of bromine (3.8 ml), 0.072 mol) in dichloromethane (200 ml) dropwise. The reaction was stirred at ambient temperature for 45 minutes, diluted with dichloromethane (200 ml) and washed with water (2×200 ml). The organic layer was dried over magnesium sulphate, and the solvent was removed in vacuo to yield a dark brown oil. Chromatography on silica eluting with a gradient of ethyl acetate in hexane (10%, 15% and 20%) afforded the title compound as a dark red oil (4 g, 25%), m/z (ES+) 202 (M30 +H, 100%). 1H NMR (250 MHz, CDCl3) δ 3.73 (3H, s), 3.78 (2H, broad s), 6.72 (2H, t, J 1.2 Hz), 7.00 (1H, q, J 1.26 Hz).

후처리

  1. washwashed with water (2×200 ml)
  2. dry with materialThe organic layer was dried over magnesium sulphate
  3. customthe solvent was removed in vacuo
  4. customto yield a dark brown oil

출처 및 근거

ORD 기록
ord-9bf65b495fb04880afd4312aed67c49e
출처 데이터셋
uspto-grants-2000_04
특허 번호
US06046195

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