[xmayer]

Can someone help me which reagents are needed to get it from benzene?

[discodermolide]

Can someone help me which reagents are needed to get it from benzene?

Not from benzene!

[Nosterius]

Hi Xmayer,

Is it part of a written exercice, or do you want to actually make it in the lab?

As Discodermolide pointed out, if you can, we would advise starting from another reagent than benzene, such as one already bearing substituent(s). Toluene, for exemple, would be a better starting point since there is already the methyl group installed on the aromatic ring.

[xmayer]

Hi Xmayer,

Is it part of a written exercice, or do you want to actually make it in the lab?

As Discodermolide pointed out, if you can, we would advise starting from another reagent than benzene, such as one already bearing substituent(s). Toluene, for exemple, would be a better starting point since there is already the methyl group installed on the aromatic ring.

Hi, it's just a written exercise. Well ok, i can get toulene with friedel-crafts alkylization.

[discodermolide]

Hi Xmayer,

Is it part of a written exercice, or do you want to actually make it in the lab?

As Discodermolide pointed out, if you can, we would advise starting from another reagent than benzene, such as one already bearing substituent(s). Toluene, for exemple, would be a better starting point since there is already the methyl group installed on the aromatic ring.

Hi, it's just a written exercise. Well ok, i can get toulene with friedel-crafts alkylization.

A Friedel-Crafts with benzene will give you a mess. I don't advise it unless you have very specific conditions.

[fledarmus]

Hi Xmayer,

Is it part of a written exercice, or do you want to actually make it in the lab?

As Discodermolide pointed out, if you can, we would advise starting from another reagent than benzene, such as one already bearing substituent(s). Toluene, for exemple, would be a better starting point since there is already the methyl group installed on the aromatic ring.

Hi, it's just a written exercise. Well ok, i can get toulene with friedel-crafts alkylization.

A Friedel-Crafts with benzene will give you a mess. I don't advise it unless you have very specific conditions.

I second this. Benzene is relatively unreactive, and every methyl group you add makes it more reactive. Toluene as it is formed will react faster than the benzene it is formed from, and you will end up with a whole mess of various alkylation patterns.

[xmayer]

Is it good if I do a diazonium salt then with E substitution a iodobenzene? Halogens has o-,p- directional so can I get a trisubstituated benzene if do the previous reaction again, finally Friedel-Crafts alkylization?

[discodermolide]

Is it good if I do a diazonium salt then with E substitution a iodobenzene? Halogens has o-,p- directional so can I get a trisubstituated benzene if do the previous reaction again, finally Friedel-Crafts alkylization?

Do you mean a Sandmeyer reaction? That would require aniline.

[Nosterius]

Xmayer,

What is your present synthetic plan for this molecule?

I would personnaly aim to make 4-methylaniline as an intermediate. From there, do you see how you can form your desired compound?

[xmayer]

 From 4-methylanaline with iodo-chloride and zinc-chloride get a 2,6-diiodo, then with Sandmeyer make iodide from amino group, maybe this?

[discodermolide]

From 4-methylanaline with iodo-chloride and zinc-chloride get a 2,6-diiodo, then with Sandmeyer make iodide from amino group, maybe this?

But you are not starting from benzene as your original post required!

[xmayer]

Hope this good for a written exercise, but revise me if not! Thank you

[fledarmus]

I think that you will find that a methyl group is a stronger o,p director than the iodo group, especially considering the size of the iodo group that you are trying to substitute next to. Would you like to try changing the order of your reactions?

[nox]

Also, your proposed sequence to make 4-methylaniline from benzene is very unlikely to work out the way you intend it to.

[Nosterius]

Xmayer: you have a nice overall scheme now. As others pointed out, you will need to start from benzene.

First, do the methylation of benzene. It will not be a clean reaction, but you can always argue that benzene vs toluene vs xylenes can be purified by distillation. Then proceed with your reactions until 4-methylaniline is obtained.

What is the better directing group between methyl, iodo and amino? Consider using it to direct your iodination reaction. If you now plan to halogenate your molecule while an amino group is present, you should protect your amino group as an acetanilide before reacting it with ICl; you will minimize side-reactions such as oxydations.