Abstract
Reactions of phenols with benzyltriphenylphosphonium tribromide in dichloromethane–methanol mixture (2:1) gave mono, di and tri brominated phenols at room temperature with high selectivity and good yields.
References
1.
(a)
Fuson
R.C.
, Reaction of Organic Compounds , New York , Wiley , 1962 , 58 , 98
2.
Norman
R.O.C.
, and
Taylor
R.
, Electrophilic Substitution in Benzenoid Compounds , New York , American Elsevier , 1965 , 130 .
3.
Dey
D.
,
Kharmawophlang
W.
,
Lakshmiprabha
T.R.
, and
Mandal
G.C.
, Tetrahedron Lett. , 1998 , 39 , 8163 .
4.
(a)
Gattaway; G. Hoyle
F.D.
, J. Chem. Soc , 1923 , 654
5.
Avramoff
M.
,
Weiss
J.
, and
Schaechter
O.
, J. Org. Chem. , 1963 , 28 , 3256 .
6.
Kajigaeshi
S.
,
Kakinami
T.
,
Yamasaki
H.
,
Fujisaki
S.
, and
Okamoto
T.
, Bull. Chem. Soc. Jpn. , 1988 , 61 , 2681 .
7.
Muathen
H.A.
, J. Org. Chem. , 1992 , 57 , 2740 .
8.
Kajigaeshi
S.
,
Kakinami
T.
,
Tokiyama
H.
,
Hirakava
T.
, and
Okamoto
T.
, Chem. Lett. , 1987 , 627 .
9.
Cristau
H.J.
,
Torreilles
E.
,
Morand
P.
, and
Cristol
H.
, Phosphorus Sulfur , 1985 , 25 , 357 –368 .
10.
Armstrong
V.W.
,
Chishti
N.H.
, and
Ramage
R.
, Tetrahedron Lett. , 1975 , 6 , 373 .
11.
Xin-teng
D.
,
Gue-bin
T.
, Synth. Commun. , 1989 , 19 , 1261 .
12.
Thampson
R.C.
, Adv. Inorg. Bioinorg. Mech. , 1986 , 4 , 65
13.
Obenland
C.O.
, J. Chem. Edu. , 1964 , 41 , 566 .
14.
Adams
R.
,
Marrei
C.S.
,
Clarke
H.T.
,
Nooller
C.R.
,
Bconant
J.
,
Whitmore
F.C.
, Organic. Syntheses , New York, John Wiley, and Sons. 1941 , Coll. Vol.1 , 194 .
15.
Cohnand
L.
, and
Schultse
F.
, Ber. 1905 , 38 , 3297 .
16.
Buckingham
J.
, and
Donagy
S.M.
, Dictionary of Organic Compounds , 5th edn, New York, Chapman, and Hall, 1982 , D-01927.
17.
Buckingham
J.
, and
Donaghy
S.M.
, Dictionary of Organic Compounds , 5th edn, New York , Chapman, and Hall , 1982 , B-023.
18.
Fojio
M.
, Bull. Chem. Soc. Jpn. , 1975 , 48 , 217 .
19.
Buckingham
J.
, and
Donaghy
S.M.
, Dictionary of Organic Compounds , 5th edn, New York, Chapman, and Hall, 1982 , B-02145.
20.
Ling
A.R.
, J. Chem. Soc. , 1989 , 55 , 585 .
21.
Datta
R.L.
, and
Bhoumik
J.C.
, J. Am. Chem. Soc. , 1921 , 43 , 309 .
22.
Buckingham
J.
, and
Donaghy
S.M.
, Dictionary of Organic Compounds , 5th edn, New York , Chapman, and Hall , 1982 , T-10204.
23.
Buckingham
J.
, and
Donaghy
S.M.
, Dictionary of Organic Compounds , 5th edn, New York , Chapman, and Hall , 1982 , D-01461.
24.
Buckingham
J.
, and
Donaghy
S.M.
, Dictionary of Organic Compounds , 5th edn, New York , Chapman, and Hall , 1982 , B-03050.
25.
Kryaski
J.
, CA, 1928 , 22 , 4120. in
Buckingham
J.
, and
Donaghy
S.M.
, Dictionary of Organic Compounds , 5th edn, New York , Chapman, and Hall , 1982, D-01940.
26.Aldrich, Catalogue Handbook of Fine Chemical , pp. 1198 , 1994 –1995
27.Aldrich, Catalogue Handbook of Fine Chemical , pp. 777 , 1994 –1995