Chrysanthemic Acid → alpha-Fluoro-3-phenoxybenzyl 3-(2-methylprop-1-enyl)-2,2-dimethylcyclopropanecarboxylate

HRID 894345Notes

Reaction equation

[CH3:1][C:2]([CH3:12])=[CH:3][CH:4]1[CH:6]([C:7]([OH:9])=[O:8])[C:5]1([CH3:11])[CH3:10].[F:13][CH:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([O:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:16]=1>>[CH3:1][C:2]([CH3:12])=[CH:3][CH:4]1[CH:6]([C:7]([O:9][CH:14]([F:13])[C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH:16]=2)=[O:8])[C:5]1([CH3:11])[CH3:10]

Participants

Reactant 2

HCID 2743Chrysanthemic Acid

HCID 13194583alpha-Fluoro-3-phenoxybenzylbromide

Product 1

HCID 12855309alpha-Fluoro-3-phenoxybenzyl 3-(2-methylprop-1-enyl)-2,2-dimethylcyclopropanecarboxylate

Procedure

This compound was prepared from 3-(2-methylprop-1-enyl)-2,2-dimethylcyclopropanecarboxylic acid and α-fluoro-3-phenoxybenzylbromide following the procedure described in Example 2 Method B. The product, a colourless oil, was characterised by pmr spectroscopy. Chemical shift δ ppm (solvent CDCl3): 1.24(6H, m, C(CH3)2); 1.70(6H, s, (CH3)2C=); about 1.9(2H, m, cyclopropyl protons); 4.93 and 5.43(1H, 2xd, J=7Hz, vinyl proton); 7.13(1H, d, J=56Hz, CHF); about 7.1(9H, m, aromatic protons).

Sources & evidence

ORD record: ord-c23d2a8e569d45c9b32c99a289d3c085
Source dataset: uspto-grants-1981_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04283414

Reaction notes

Loading…