Author Topic: 1,2-Diphenylethyl Chloride  (Read 642 times)

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1,2-Diphenylethyl Chloride
« on: September 22, 2003, 09:18:00 AM »
Would anyone know the CAS# for this, properties, etc.?
I don't have a way to the local university library at the moment, and my STN Easy account is overdue.


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adaptable(?) synth for this one
« Reply #1 on: October 04, 2003, 11:57:00 AM »
I found an interesting procedure for 2-(4-Bromophenyl)-1-chloro-1-phenylethane, which is quite the same as 1,2-diphenylethyl chloride, only with a bromine atom added.

The synthesis is taken from

'Reaktionen und Synthesen im organisch-chemischen Praktikum und Forschungslaboratorium' by Lutz Friedjan Tietze und Theophil Eicher, 2. neub. Aufl, - Georg Thieme Verlag Stuttgart - New York, p. 224, 'K-41 2-(4-phenyl)-1-chlor-1-phenylethan'

- btw, indeed a good book ;)

I'll be decent and present it in English:

"To a cooled solution (ice-rock salt bath) of 17.2g (0.10 mol) p-bromoaniline in 60 ml 5 M hydrochloric acid is dripped with stirring 7.00g (0.10 mol) sodium nitrite in 35 ml water, ensuring that the temperature of the reaction mixture does not rise above 5 °C (check completion of diazotation with starch-iodide paper, add some more nitrite if necessary). The diazotation solution is brought up to a pH of 4-5 by adding 14.3 g sodium bicarbonate in portions and then is dripped within 10 min while stirring to a solution of 10.4 g (0.10 mol) styrene and 4.00 g (25.0 mmol) copper(II)-chloride dihydrate in 100 ml acetone. A slow evolution of nitrogen starts which gets more vigorous only after 1 h, it is finished after 15 h.

100 ml ether are added, the dark organic phase is removed and the aqueous phase extracted twice with 50 ml ether each. After drying the ether phase with MgSO4 the solvent is removed in vacuo and the residual brown oil is made to crystalize by scratching with a little petrolether (b.p. 50 - 70 °C): 16.9 g (57%), m.p. 81 - 82 °C; from ethanol slightly brownish needles, m.p. 87 - 88 °C.

Note: The styrene (b.p. 12mm 33-34 °C) used is to be distilled over hydrochinone and to be stored stabilized with hydrochinone.

[..] Radical addition of aromatic compounds to activated alkenes catalyzed by Cu(I) (Meerwein-arylation) [to avoid confusion, the procedure indeed states to use Cu(II)-chloride]"

Regular aniline would most likely bee what we want, I see no reason why it couldn't react. The diazonium ion should be rather more stable as there is no electronegative bromine sucking electrons away from it, on the other hand there might be less stabilization by resonance. Also, more stability might mean less reactivity, the reaction takes long enough anyway.