Novel DOM synthesis
Jan 4, 2018 11:15:18 GMT
Post by rayancaleb on Jan 4, 2018 11:15:18 GMT
Hello.
DOM has always been notoriously difficult to prepare because of the somewhat odd precursors required and the formylation step needed to make the benzaldehyde. After the discussion in the serious chemistry forum about the two new active compounds DOMCl and DOMOM (Post 486635 (Rhodium: "Two new DOM analogs made and evaluated", Serious Chemistry)), the idea for the new DOM synthesis spawned.
they chloromethylate this in very high yields(70.8%). As debated earlier chloromethylation is not a very nice procedure, because of the complicated set up, noxious and toxic gasses involved. Bromomethylation ala Lego looks much nicer(see Post 475109 (Lego: "Amphetamines/PEAs w/o benzaldehyde or nitroethane", Novel Discourse), as no gassing is required. I suppose the same yields can be expected from the bromomethylation as the chloromethylation. After the isolation of the -most likely nasty/toxic- DOMCl the next step can commence.
As the whole DOM molecule is quite stable there are many ways of dehalogenate this. Many reducing agents will do the job[1]. The most common being lithium aluminium hydride[2]. Another powerful reagent, which reduces primary, secondary, tertiary, allylic, vinylic, aryl and neopentyl halides, is a complex formed from lithium trimethoxyaluminium hydride LiAlH(OMe)3 and CuI[3]. A milder reducing agent is Sodium Borohydride, NaBH4, in a dipolar aprotic solvent such as Me2SO (DMSO), DMF or sulfolane[4], which at room temperature or above reduces primary, secondary, and some tertiary[5] halides in good yield without affecting other functional groups that would be reduced by LiAlH4.
thanks
more details:
Gadget Animation
DOM has always been notoriously difficult to prepare because of the somewhat odd precursors required and the formylation step needed to make the benzaldehyde. After the discussion in the serious chemistry forum about the two new active compounds DOMCl and DOMOM (Post 486635 (Rhodium: "Two new DOM analogs made and evaluated", Serious Chemistry)), the idea for the new DOM synthesis spawned.
they chloromethylate this in very high yields(70.8%). As debated earlier chloromethylation is not a very nice procedure, because of the complicated set up, noxious and toxic gasses involved. Bromomethylation ala Lego looks much nicer(see Post 475109 (Lego: "Amphetamines/PEAs w/o benzaldehyde or nitroethane", Novel Discourse), as no gassing is required. I suppose the same yields can be expected from the bromomethylation as the chloromethylation. After the isolation of the -most likely nasty/toxic- DOMCl the next step can commence.
As the whole DOM molecule is quite stable there are many ways of dehalogenate this. Many reducing agents will do the job[1]. The most common being lithium aluminium hydride[2]. Another powerful reagent, which reduces primary, secondary, tertiary, allylic, vinylic, aryl and neopentyl halides, is a complex formed from lithium trimethoxyaluminium hydride LiAlH(OMe)3 and CuI[3]. A milder reducing agent is Sodium Borohydride, NaBH4, in a dipolar aprotic solvent such as Me2SO (DMSO), DMF or sulfolane[4], which at room temperature or above reduces primary, secondary, and some tertiary[5] halides in good yield without affecting other functional groups that would be reduced by LiAlH4.
thanks
more details:
Gadget Animation