Author Topic: Cl-benzene --> P2P  (Read 2583 times)

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  • Guest
Cl-benzene --> P2P
« on: June 10, 2002, 10:20:00 AM »
this rnx doesn't exactly use chlorobenzene, instead a
substituted chlorobenzene is used. this 2,6-dichlorotoluene
is chlorobenzene with 2 ringsubstituents(Cl & CH3) in
both ortho positions. and 1-(3-Chloro-2-methylphenyl)propanone
is simply P2P with the same 2 ringsubstituents(Cl & CH3).

1-(3-Chloro-2-methylphenyl)propanone (19)

A solution of 3-bromo-2-methoxypropene (12.6g, 83.1mmol) in
benzene was added to a solution of the mono-Grignard reagent[15]
prepared from 2,6-dichlorotoluene (23.8g, 148mmol) in dry THF at
0°C. The reaction mixture was then stirred at room temperature
for 18h. The mixture was then hydrolyzed with H2SO4/H2O (1:1)
until all solids dissolved. It was then extracted with CH2Cl2.
The organic layer was washed, dried, and evaporated to give the
intermediate product 21. This was hydrolyzed by stirring in 1N
HCl for 1h. The reaction mixture was then extracted with CH2Cl2,
washed, dried, and evaporated. The crude product was chromato-
graphed on silica gel using CH2Cl2:hexane 1:1 as eluent to give the
ketone(19) 8.8g (58%), identical (1H NMR, IR, MS) to the previously
obtained sample.

[15] j org chem, 1984 49: 2534; r h mitchell, y -h lai

j org chem, 1996 61(3): 935-940
"Synthesis and Diatropicity of trans-2',5',10b,10c-
Tetramethylfurano[3,4-e]-10b,10c-dihydropyrene. A Valence
Isomerization To Form a Novel Isoannulenofuran at the Expense
of Two Benzene and One Furan Rings"; Yee-Hing Lai, Pu Chen


  • Guest
How is 3-bromo-2-methoxypropene synthesized?
« Reply #1 on: June 10, 2002, 01:02:00 PM »
How is 3-bromo-2-methoxypropene synthesized? It is not sold by Aldrich.


  • Guest
Re: 3-bromo-2-methoxypropene
« Reply #2 on: June 10, 2002, 01:36:00 PM »
> How is 3-bromo-2-methoxypropene synthesized?

i've send the pdf over to you, perhaps in the
paper is something about that ?