P-Anisidine → 2-Bromo-4-methoxyaniline

HRID 1003255ノート

反応式

HRID 1003255 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

HCID 108996712-Bromo-4-methoxyaniline収率 25%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒3 回HCID 8058Hexane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-9bf65b495fb04880afd4312aed67c49e
出典データセット
uspto-grants-2000_04
特許番号
US06046195

反応ノート

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