3-Chloro-2-methyl-1-propene → 1-[3,5-Diiodo-4-(2-methyl-allyloxy)-phenyl]cyclopropane-carboxylic acid methyl ester

HRID 1008794

반응식

HRID 1008794 반응식
[CH3:1][O:2][C:3]([C:5]1([C:8]2[CH:13]=[C:12]([I:14])[C:11]([OH:15])=[C:10]([I:16])[CH:9]=2)[CH2:7][CH2:6]1)=[O:4].Cl[CH2:18][C:19]([CH3:21])=[CH2:20].C([O-])([O-])=O.[K+].[K+]>CC(C)=O.[Na+].[I-]>[CH3:1][O:2][C:3]([C:5]1([C:8]2[CH:9]=[C:10]([I:16])[C:11]([O:15][CH2:20][C:19]([CH3:21])=[CH2:18])=[C:12]([I:14])[CH:13]=2)[CH2:7][CH2:6]1)=[O:4]

참가 물질

6

반응물 3

HCID 112413-Chloro-2-methyl-1-propeneHCID 11430Potassium CarbonateHCID 591292811-(4-Hydroxy-3,5-diiodo-phenyl)-cyclopropanecarboxylic acid methyl ester

생성물 1

HCID 591292181-[3,5-Diiodo-4-(2-methyl-allyloxy)-phenyl]cyclopropane-carboxylic acid methyl ester수율 97.6%

시약·촉매·용매 2

HCID 5238Sodium Iodide촉매HCID 180Acetone용매

반응 조건

온도
20 °C

실험 절차

A mixture of 1-(4-hydroxy-3,5-diiodo-phenyl)-cyclopropanecarboxylic acid methyl ester (3.2 g, 7.2 mmol), 3-chloro-2-methyl-propene (1.0 g, 11 mmol), K2CO3 (1.2 g, 8.6 mmol), NaI (0.1 g, 0.7 mmol) in acetone (20 mL) was stirred at 20° C. overnight. The solid was filtered off and the filtrate was concentrated under vacuum to give 1-[3,5-diiodo-4-(2-methyl-allyloxy)-phenyl]-cyclopropane-carboxylic acid methyl ester (3.5 g, 97%). 1H NMR (300 MHz, CDCl3) δ 7.75 (s, 2 H), 5.26 (s, 1 H), 5.06 (s, 1 H), 4.38 (s, 2 H), 3.65 (s, 3 H), 1.98 (s, 3H), 1.62-1.58 (m, 2 H), 1.18-1.15 (m, 2 H).

후처리

  1. filtrationThe solid was filtered off
  2. concentrationthe filtrate was concentrated under vacuum

출처 및 근거

ORD 기록
ord-520beca3f3184df79c7d1d865cd55657
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07973038B2

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