Author Topic: 3-(2-Bromoethyl)indole Synthesis  (Read 5047 times)

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3-(2-Bromoethyl)indole Synthesis
« on: November 01, 2001, 10:53:00 PM »
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Indole derivatives.  C.  Synthesis of w-(3-indolyl)alkyl bromides.    
Eryshev, B. Ya.; Dubinin, A. G.; Buyanov, V. N.; Suvorov, N. N.   
Khim. Geterotsikl. Soedin.  (1974),   (11),  1493-5. 
CODEN: KGSSAQ  Journal  written in Russian.   
CAN 82:125216    AN 1975:125216   

The indolylalkyl bromides I (R = Br; n = 2,3,4,10) were prepd. by Hunsdiecker bromination-decarboxylation
 of the Hg salts of I (R = CO2H).  Alternately, I (R = Br; n = 3,4) were prepd. by reaction of I (R = HO)
with PBr3 in Et2O. 

Hunsdiecker Reaction
Preparation of aklyl halogenides from carboxylic acids.
HgO or Ag2O is used as catalyst. The reaction is via a radical mechanism and must be lightened.

Hunsdiecker Reaction (Borodine Reaction)

C. Hunsdiecker, H. Hunsdiecker and E. Vogt, U.S. pat. 2,176,181 (1939)
H. Hunsdiecker and C Hunsdiecker, Ber. 75, 291 (1942)
A. Borodine, Ann.119, 121 (1861)
R. G. Johnson and R. K. Ingham, Chet. Reus. 56, 219 (1956)
C. V. Wilson, Organic Reactions 9, 341 (1957)
P. I. Abell J. Org. Chem. 22, 769 (1957)
V. Franzen, Chem. Ztg. 81, 138 (1957)
J. W. Wilt and D. D. Oathoudt, J. Ore. Chem. 23 18 (1958)
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S. J. Cristol and W. C. Firth Jr., J. Org. Chem. 26 280 (1961)
D. H. R. Barton and E. P. Serebryakov, Proc. Chem. Soc. 1962, 309
D. E. Applequist and N. D. Werner, J. Org. Chem. 28, 48 (1963)
F. W. Baker, H. D. Holtz and L. M. Stock, J. Org. Chem. 28, 514 (1963)
J. A. Davis, J. Herynk, S.Carroll, J. Bunds, D. Johnson, J. Org. Chem. 30, 415 (1965)

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