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

HRID 272694

반응식

HRID 272694 반응식
[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]

참가 물질

7

반응물 3

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

생성물 1

HCID 584754055-Chloro-2-iodo-4-methylaniline수율 63.5%

시약·촉매·용매 3

HCID 887Methanol용매HCID 3283Diethyl Ether용매HCID 6344Dichloromethane용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-4717a9b5d6464228960f5169b18f2799
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07456169B2

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