Daphuk_up (Hive Bee)
04-28-04 17:48
No 503640
       Grignard and 2C-B     

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.smile

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.
Drug Chemists are Ta to a good Sm. 		 
 
 
 
    Rhodium
(Chief Bee)
04-29-04 06:45
No 503739
       Grignard incompabilities     

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.
The Hive - Clandestine Chemists Without Borders 		 
 
 
 
    Daphuk_up
(Hive Bee)
04-29-04 22:23
No 503910
       SWID thanks you for the clarification.     

SWID thanks you for the clarification. smile

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
Drug Chemists are Ta to a good Sm. 		 
 
 
 
    Rhodium
(Chief Bee)
04-30-04 07:19
No 504007
       2,5-dimethoxybromobenzene grignard     

Regarding the formation of 2,5-dimethoxybromobenzene grignard, read the following:

../rhodium /2cbde.html
Post 354784 (Rhodium: "Tips & Tricks regarding dimethoxybenzene Grignards", Novel Discourse)
The Hive - Clandestine Chemists Without Borders