quick hit pure curiosity question (no search engine to satisfy monkey urges):
Will 2c-b form a grignard reagent (specific to the aromatic bromine)? Will dripping an ethereal solution of 2c-b into the grignard addition product of ethyl bromide produce 2c-e?
Thanks. :)
EDIT: Found that grignard reagents react with nitriles, but what about terminal nitrogens saturated with either hydrogen or oxygen? (ie, 2c-b or 4-bromo-2,5-dimethoxy-nitroethane?) SWID is unsure if the double carbon bond in a styrene would have any effect or not.
Will 2c-b form a grignard reagent (specific to the aromatic bromine)? Will dripping an ethereal solution of 2c-b into the grignard addition product of ethyl bromide produce 2c-e?
No and no. The grignard reagent is incompatible with the amine.
Found that grignard reagents react with nitriles, but what about terminal nitrogens saturated with either hydrogen or oxygen? (ie, 2c-b or 4-bromo-2,5-dimethoxy-nitroethane?) SWID is unsure if the double carbon bond in a styrene would have any effect or not.
Grignard reagents can usually not be made from compounds containing any of the following groups: nitriles, acids, carbonyl functions (ketone/aldehyde/ester/amide/anhydride) and any functional group containing -NO2, -OH, -SH, or -NH groups.
SWID thanks you for the clarification. :)
He supposes the best route then would be:
1. monobromination of 2,5-dimethoxybenzene
2. grignard reaction with ethyl bromide
3. gatterman formylation
4. subsequent condensation with nitromethane and reduction(s) to afford phenethylamine
Regarding the formation of 2,5-dimethoxybromobenzene grignard, read the following:
https://www.thevespiary.org/rhodium/Rhodium/chemistry/2cbde.html (https://www.thevespiary.org/rhodium/Rhodium/chemistry/2cbde.html)
Post 354784 (https://www.thevespiary.org/talk/index.php?topic=12028.msg35478400#msg35478400)
(Rhodium: "Tips & Tricks regarding dimethoxybenzene Grignards", Novel Discourse)