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

HRID 1505087

Reaction equation

[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]

Participants

Conditions

Temperature: 20 °C

Procedure

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, 3 H), 1.62-1.58 (m, 2 H), 1.18-1.15 (m, 2 H).

Workup

filtrationThe solid was filtered off
concentrationthe filtrate was concentrated under vacuum

Sources & evidence

ORD record: ord-6a9935986be1425581189bcfd2d22f4f
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09216969B2

Linked notes

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