✦ LIBER ✦

2-fluoro- and 5-fluoro-3,4-dimethylphenethylamine derived from claisen rearrangement products

✍ Scribed by Michael T. Clark; Duane D. Miller

Book ID: 104228869
Publisher: Elsevier Science
Year: 1985
Tongue: French
Weight: 129 KB
Volume: 26
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)98717-3

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✦ Synopsis

The Claisen rearrangement of 2-allyloxy-3-fluoroanisole followed by methylation provided the para-rearranged product along with the unexpected 3-(3,4-dimethoxy-2fluorophenyl)-I-propene.

A new method for the synthesis of 3,4-dimethoxy-5-fluorophenethylamine ( 1 ) was sought in order to obtain large quantities of it since a previously reported sequence provided an overall low yield of 1. In the previous sequence the low yielding step involved a photochemical-Schiemann reaction of 5-nitrovanillin and scale up of this previous scheme would likely be very difficult.' As a new alternative , the Claisen rearrangement and methylation of 2-allyloxy-3-fluoroanisole 2 ( 2 1 and subsequent ozonolysis, oxime formation and reduction was projected for the synthesis of 1 as illustrated below.

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