Abstract
2-Iodoxybenzoic acid (IBX) has been shown to react with alkyl halides in the presence of tetraethyl ammonium bromide to give 2-iodobenzoate esters. Most of the monohalides and dihalides reacted easily with moderate to good yields. The 2-iodobenzoate esters containing other functional groups can offer further synthetic uses. The 2-iodobenzoic acid can be recycled easily and oxidised to IBX again.
References
1.
Satam V.
,
Harad A.
,
Rajule R.
, and
Pati H.
, Tetrahedron , 2010 , 66 , 7659 .
2.
Duschek A.
, and
Kirsch S.F.
, Angew. Chem. Int. Ed. , 2011 , 50 , 1524 .
3.
Zhdankin V.V.
, J. Org. Chem. , 2011 , 76 , 1185 .
4.
Pan Z.
,
Liu X.
, and
Liang Y.
, Tetrahedron Lett. , 2004 , 45 , 4101 .
5.
Pan Z.
,
Liu X.
,
Liu W.
, and
Liang Y.
, Synthesis , 2005 , 437 .
6.
Takahashi M.
,
Ogiku T.
,
Okamura K.
,
Da-Te T.
,
Ohmizu H.
,
Kondo K.
, and
Iwasaki T.
, J. Chem. Soc., Perkin Trans. 1 , 1993 , 1473 .
7.
Surry D.S.
,
Su X.
,
Fox D.J.
,
Franckevicius V.
,
Macdonald S.J.F.
, and
Spring D.R.
, Angew. Chem. Int. Ed. , 2005 , 44 , 1870 .
8.
Zhdankin V.V.
,
Koposov A.Y.
,
Litvinov D.N.
,
Ferguson M.J.
,
McDonald R.
,
Luu T.
, and
Tykwinski R.R.
, J. Org. Chem. , 2005 , 70 , 6484 .
9.
Fontaine P.
,
Chiaroni A.
,
Masson G.
, and
Zhu J.
, Org. Lett. , 2008 , 10 , 1509 .
10.
Drouet F.
,
Fontaine P.
,
Masson G.
, and
Zhu J.
, Synthesis , 2009 , 1370 .
11.
Bhalerao D.S.
,
Mahajan U.S.
,
Chaudhari K.H.
, and
Akamanchi K.G.
, J. Org. Chem. , 2006 , 72 , 662 .
12.
Bellale E.V.
,
Bhalerao D.S.
, and
Akamanchi K.G.
, J. Org. Chem. , 2008 , 73 , 9473 .
13.
Dakka J.
,
Sasson Y.
,
Khawaled K.
,
Bram G.
, and
Loupy A.
, J. Chem. Soc., Chem. Commun. , 1991 , 853 .
14.
Chevallet P.
,
Garrouste P.
,
Malawska B.
, and
Martinez J.
, Tetrahedron Lett. , 1993 , 34 , 7409 .
15.
Jagdale S.J.
,
Patil S.V.
, and
Salunkhe M.M.
, Synth. Commun , 1996 , 26 , 1747 .
16.
Wagenknecht J.H.
,
Baizer M.M.
, and
Chrtuna J.L.
, Synth. Commun , 1972 , 2 , 215 .
17.
Shaw J.E.
,
Kunerth D.C.
, and
Sherry J.J.
, Tetrahedron Lett. , 1973 , 14 , 689 .
18.
Moorthy J.N.
,
Singhal N.
, and
Senapati K.
, Tetrahedron Lett. , 2006 , 47 , 1757 .
19.
Kabalka G.W.
,
Wang L.
, and
Pagni R.M.
, Green Chemistry , 2001 , 3 , 261 .
20.
Campbell M.J.
, and
Johnson J.S.
, Org. Lett. , 2007 , 9 , 1521 .
21.
Frigerio M.
,
Santagostino M.
, and
Sputore S.
, J. Org. Chem. , 1999 , 64 , 4537 .
22.
Robert J.
,
Boeckman K.
,
Shao P.
, and
Mullins J.J.
, Organic syntheses. Coll. Vol. , 2004 , 10 , 696 .
23.
Zhdankin V.V.
,
Koposov A.Y.
,
Netzel B.C.
,
Yashin N.V.
,
Rempel B.P.
,
Ferguson M.J.
, and
Tykwinski R.R.
, Angew. Chem. Int. Ed. , 2003 , 42 , 2194 .
24.
Zhdankin V.V.
,
Litvinov D.N.
,
Koposov A.Y.
,
Luu T.
,
Ferguson M.J.
,
McDonald R.
, and
Tykwinski R.R.
, Chem. Commun. , 2004 , 106 .
25.
Umetsu K.
, and
Asao N.
, Tetrahedron Lett. , 2008 , 49 , 7046 .
26.
Farooq U.
,
Schäfer S.
,
Shah A.-u.-H.A.
,
Freudendahl D.M.
, and
Wirth T.
, Synthesis , 2010 , 1023 .
27.
Jean M.
,
Renault J.
,
van de Weghe P.
, and
Asao N.
, Tetrahedron Lett. , 2010 , 51 , 378 .
28.
Hashmi A.S.K.
,
Ruppert T.L.
,
Knöfel T.
, and
Bats J.W.
, J. Org. Chem. , 1997 , 62 , 7295 .
29.
Beckwith A.L.J.
, and
Meijs G.F.
, J. Org. Chem. , 1987 , 52 , 1922 .
30.
Strain W.H.
,
Plati J.T.
, and
Warren S.L.
, J. Am. Chem. Soc. , 1942 , 64 , 1436 .
31.
Wessig P.
, and
Matthes A.
, J. Am. Chem. Soc. , 2011 , 133 , 2642 .
