[kanonsviel]

Is it possible to make an aminophenol first then use it attack another benzene ring in some way?

[ooosh]

Maybe you can synthesize it by nucleophilic aromatic substitution ,use p-nitrochlorobenzene and phenol as starting materials under basic condition(you can use K2CO3 as base),you will get 4-nitrophenyl ether,then reduce the nitro group you will get the compound you want.
The only problem is how can you synthesize p-nitrochlorobenzene by bezene.

[discodermolide]

Is it possible to make an aminophenol first then use it attack another benzene ring in some way?

Nitrate benzene
reduce to aniline
do a Sandmeier reaction with a halogen source = halo benzene
make a borinate ester

Halogenate the aniline (will need protection)
Do a Suzuki coupling to combine the phenyl rings
Finished

[ooosh]

Is it possible to make an aminophenol first then use it attack another benzene ring in some way?

Nitrate benzene
reduce to aniline
do a Sandmeier reaction with a halogen source = halo benzene
make a borinate ester

Halogenate the aniline (will need protection)
Do a Suzuki coupling to combine the phenyl rings
Finished

Suzuki product will not be an ether but a biphenyl .

[SVXX]

Why not use simple Williamson synthesis?
Suppose I have two benzene molecules. Those are the only C-sources I need.

For the first benzene :
Step I - Nitration.
Step II - Reduction of -NO₂ to -NH₂.
Step III - Electrophilic aromatic substitution to introduce a halogen group in the para position.

For the second benzene :
Step I - Sodium phenoxide synthesis. Sulfonate the benzene ring with an EAS reaction, then treat the sodium salt of benzene sulfonate with hot and fused NaOH. We obtain PhONa.

Now we perform Williamson's synthesis on the two rings.

                            (Basic Medium)
H₂N-Ph-X  + PhONa  -------------->  H₂N-Ph-OPh + NaX
                             Cu(catalyst)

[discodermolide]

Is it possible to make an aminophenol first then use it attack another benzene ring in some way?

Nitrate benzene
reduce to aniline
do a Sandmeier reaction with a halogen source = halo benzene
make a borinate ester

Halogenate the aniline (will need protection)
Do a Suzuki coupling to combine the phenyl rings
Finished

Suzuki product will not be an ether but a biphenyl .

Sorry my mistake!

[kanonsviel]

Maybe you can synthesize it by nucleophilic aromatic substitution ,use p-nitrochlorobenzene and phenol as starting materials under basic condition(you can use K2CO3 as base),you will get 4-nitrophenyl ether,then reduce the nitro group you will get the compound you want.
The only problem is how can you synthesize p-nitrochlorobenzene by bezene.

That's a nice hint  , but if only I could ignore the probability of multi-substitution...besides, I'm not quite sure whether phenol is a strong enough nucleophile to attack the p-nitrochlorobenzene.

[ooosh]

Don't worry about the reactivity of p-nitrochlorobenzene.there will be a Meisenheimer complex (http://en.wikipedia.org/wiki/Meisenheimer_complex)in the reaction to promote the substitution.

[ooosh]

I find something more useful ,which is more powerful to prove my method : http://en.wikipedia.org/wiki/4-Nitrochlorobenzene

4-Nitrochlorobenzene is an intermediate in the preparation of a variety of derivatives, including 4-chloroaniline, 4-nitrophenol, 4-nitroanisole, 4-nitroaniline, 2,4-dinitrochlorobenzene, and 3,4-dichloronitrobenzene.
These reactions mainly involve the nucleophilic displacement of chloride . The electron-withdrawing nature of the appended nitro-group makes the benzene ring especially susceptible to nucleophilic aromatic substitution, unlike related chlorobenzene.

[kanonsviel]

Well, actually I was not worrying the activity of 4-nitrochlorobenzene but that of the phenol
http://www2.chemistry.msu.edu/faculty/reusch/VirtTxtJml/benzrx2.htm#benz11
It gives me an impression that a mono-nitrochlorobenzene might need a strong base to undergo the nucleophilic aromatic substitution reaction (the bases become weaker and temperature milder as the nitro substituents increase)
However, that is also a helpful hint, if an aniline is able to do the job, a phenol might be able to do it as well...
Thanks for your help

[ooosh]

My pleasure!