3-Chloro-4-methylaniline → 5-Chloro-2-iodo-4-methylaniline

HRID 272694ノート

反応式

HRID 272694 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[CH3:9])[NH2:5].[I:10](Cl)(=O)=O.I(Cl)(=O)=O.C([N+](C)(C)C)C1C=CC=CC=1.C([O-])([O-])=O.[Ca+2]>C(Cl)Cl.CO.CCOCC>[Cl:1][C:2]1[C:8]([CH3:9])=[CH:7][C:6]([I:10])=[C:4]([CH:3]=1)[NH2:5]

参加物

7

反応物 3

HCID 72553-Chloro-4-methylanilineHCID 10112Calcium CarbonateHCID 56924451Trimethylbenzylammonium Dichloroiodate

生成物 1

HCID 584754055-Chloro-2-iodo-4-methylaniline収率 63.5%

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 3283Diethyl Ether溶媒HCID 6344Dichloromethane溶媒

実験手順

3-Chloro-4-methylaniline (1.50 g, 10.6 mmol) and benzyltrimethylammonium dichloroiodate (4.60 g, 13.2 mmol) were dissolved in CH2Cl2 (50 mL) and MeOH (20 mL), then CaCO3 (3.10 g, 31.0 mmol) was added and the reaction stirred at room temperature overnight. The reaction was diluted with Et2O (200 mL), filtered through Celite®, and concentrated. The crude material was purified by column chromatography using 97.5/2.5 hexane/EtOAc, giving the product (1.80 g, 63%) as light tan solids. MS (DCI) m/e 268 and 270 (M+H)+; 1H NMR (300 MHz, CDCl3) δ 7.48 (s, 1H), 6.76 (s, 1H), 4.00 (v br s, 2H), 2.22 (s, 3H).

後処理

  1. filtrationfiltered through Celite®
  2. concentrationconcentrated
  3. customThe crude material was purified by column chromatography

出典と根拠

ORDレコード
ord-4717a9b5d6464228960f5169b18f2799
出典データセット
uspto-grants-2008_11
特許番号
US07456169B2

反応ノート

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