7.20 (s, 1H), 6.75 (d, J = 8.7 Hz, 1H), 3.80 (s, 3H), 2.19 (s, 3H),
2.13 (s, 3H); 13C NMR (75 MHz, CDCl3) d 168.4, 154.9, 130.6,
127.3, 123.6, 119.2, 110.3, 55.7, 24.4, 16.3; IR (KBr) u 3248, 2952,
1650, 1572, 1505, 1398, 1231, 1035, 881, 765 cm-1; HRMS (EI)
Calculated for C10H13NO2 (M+) 179.0946, found 179.0947.
6.0 Hz, 1H), 2.14 (s, 3H), 1.31 (d, J = 6.0 Hz, 6H); 13C NMR
(75MHz, CDCl3) d 168.6, 154.8, 131.1, 122.1 (2C), 116.5 (2C),
70.5, 24.3, 22.1 (2C); IR (KBr) u 3267, 2925, 1656, 1613, 1560,
1510, 1376, 1242, 1114, 837, 771 cm-1; HRMS (EI) Calculated for
C11H15NO2 (M+) 193.1103, found 193.1103.
4-Methoxy-2-fluoroacetanilide (3d). Yield (61%), white solid,
mp 105–107 ◦C, 1H NMR (300 MHz, CDCl3) d 8.01 (t, J = 9.0 Hz,
1H), 7.29 (br s, 1H, NH), 6.66–6.62 (m, 2H), 3.76 (s, 3H), 2.17 (s,
3H); 13C NMR (75 MHz, CDCl3) d 168.3, 156.9, 153.8 (d, J =
242.1 Hz), 123.7, 119.5, 109.5, 101.9 (d, J = 23.0 Hz), 55.8, 24.4;
IR (KBr) u 3247, 2972, 1656, 1602, 1544, 1509, 1372, 1214, 1103,
1034, 942, 839 cm-1; HRMS (EI) Calculated for C9H10NO2F (M+)
183.0696, found 183.0698.
4-(2-Hydroxy-ethoxy)acetanilide (3k). Yield (33%), white
◦
1
solid, mp 118–119 C, H NMR (300 MHz, d-DMSO) d 9.79
(br s, 1H, NH), 7.46 (d, J = 9.0 Hz, 2H), 6.85 (d, J = 9.0 Hz, 2H),
4.86 (t, J = 4.8 Hz, 1H, OH), 3.92 (t, J = 4.8 Hz, 2H), 3.69 (t, J =
4.8 Hz, 2H), 1.99 (s, 3H);13C NMR (75 MHz, d-DMSO) d 167.9,
154.5, 132.6, 120.7 (2C), 114.4 (2C), 69.7, 59.7, 23.3; IR (KBr) u
3426, 3069, 3005, 2935, 1678, 1595, 1573, 1021, 861 cm-1; HRMS
(EI) Calculated for C10H13NO3 (M+) 195.0895, found 195.0899.
4-Methoxy-2-chloroacetanilide (3e). Yield (63%), white solid,
◦
1
mp 114–115 C, H NMR (300 MHz, CDCl3) d 8.13 (d, J =
9.0 Hz, 1H), 7.40 (br s, 1H, NH), 6.92 (d, J = 2.4 Hz, 1H), 6.81
(dd, J = 9.0, 2.4 Hz, 1H), 3.77 (s, 3H), 2.20 (s, 3H); 13C NMR
(75 MHz, CDCl3) d 168.3, 156.5, 128.0, 124.3, 123.5, 114.6, 113.3,
55.8, 24.7; IR (KBr) u 3289, 2925, 1658, 1534, 1400, 1280, 1049,
883, 813, 606 cm-1; HRMS (EI) Calculated for C9H10NO235Cl (M+)
199.0400, found 199.0392.
Acknowledgements
We gratefully acknowledge the National Natural Science Foun-
dation of China (No. 20602033 and No. 21072180) and National
Basic Research Program of China (2006CB922001) for the finan-
cial support.
4-Methoxy-2-bromoacetanilide (3f). Yield (64%), white solid,
Notes and references
◦
1
mp 124–126 C, H NMR (300 MHz, CDCl3) d 8.11 (d, J =
9.0 Hz, 1H), 7.36 (br s, 1H, NH), 7.09 (d, J = 2.7 Hz, 1H), 6.87
(dd, J = 9.0, 2.7 Hz, 1H), 3.78 (s, 3H), 2.21 (s, 3H); 13C NMR
(75 MHz, CDCl3) d 168.2, 156.7, 129.2, 123.7, 117.6, 114.7, 114.0,
55.8, 24.6; IR (KBr) u 3300, 2932, 1660, 1602, 1520, 1340, 1278,
1037, 877, 575 cm-1; HRMS (EI) Calculated for C9H10NO281Br
(M+) 244.9874, found 244.9880.
1 For recent reviews of hypervalent iodine reagents in oxidation reaction,
see: (a) M. Uyanik and K. Ishihara, Chem. Commun., 2009, 2086; (b) T.
Dohi and Y. Kita, Chem. Commun., 2009, 2073; (c) V. V. Zhdankin
and P. J. Stang, Chem. Rev., 2008, 108, 5299; (d) M. Ochiai and K.
Miyamoto, Eur. J. Org. Chem., 2008, 4229; (e) V. V. Zhdankin, Sci.
Synth., 2007, 31a, 161 chapter 31.4.1; (f) T. Wirth, Angew. Chem.,
Int. Ed., 2005, 44, 3656; (g) R. M. Moriarty, J. Org. Chem., 2005,
70, 2893; (h) H. Tohma and Y. Kita, Adv. Synth. Catal., 2004, 346,
111; (i) Hypervalent Iodine Chemistry (Ed.: T. Wirth), Springer-Verlag,
Berlin, 2003; (j) V. V. Zhdankin and P. J. Stang, Chem. Rev., 2002, 102,
2523.
2 For recent examples of hypervalent iodine compounds in C–O bonds
formation, see: (a) J. Yu, J. Tian and C. Zhang, Adv. Synth. Catal., 2010,
352, 531; (b) M. Uyanik, T. Yasui and K. Ishihara, Angew. Chem., Int.
Ed., 2010, 49, 2175; (c) Y. Gu and K. Xue, Tetrahedron Lett., 2010, 51,
192; (d) R. Fan, Y. Sun and Y. Ye, Org. Lett., 2009, 11, 5174; (e) T. Dohi,
A. Maruyama, N. Takenaga, K. Senami, Y. Minamitsuji, H. Fujioka,
S. B. Caemmerer and Y. Kita, Angew. Chem., Int. Ed., 2008, 47, 3787;
(f) T. Dohi, K. Takenaga, A. Goto, A. Maruyama and Y. Kita, Org.
Lett., 2007, 9, 3129; (g) K. Hata, H. Hamamoto, Y. Shiozaki, S. B.
Ca¨mmerer and Y. Kita, Tetrahedron, 2007, 63, 4052; (h) T. Dohi, A.
Maruyama, M. Yoshimura, K. Morimoto, H. Tohma and Y. Kita,
Angew. Chem., Int. Ed., 2005, 44, 6193; (i) H. Hamamoto, K. Hata, H.
Nambu, Y. Shiozaki, H. Tohma and Y. Kita, Tetrahedron Lett., 2004,
45, 2293.
3 For recent examples of hypervalent iodine compounds in C–N bond
formation: (a) W. Zhou, L. Zhang and N. Jiao, Angew. Chem., Int. Ed.,
2009, 48, 7094; (b) R. Fan, W. Li, D. Pu and L. Zhang, Org. Lett., 2009,
11, 1425; (c) R. C. F. Jones, S. C. Yau, J. N. Iley, J. E. Smith, J. Dickson,
M. R. J. Elsegood, V. McKee and S. J. Coles, Org. Lett., 2009, 11, 1519;
(d) R. Fan, L. Wang, Y. Ye and J. Zhang, Tetrahedron Lett., 2009, 50,
3857; (e) R. Fan, D. Pu, J. Gan and B. Wang, Tetrahedron Lett., 2008,
49, 4925; (f) H. Liang and M. A. Ciufolini, J. Org. Chem., 2008, 73,
4299; (g) T. Dohi, A. Maruyama, Y. Minamitsuji, N. Takenaga and
Y. K i t a , Chem. Commun., 2007, 1224; (h) Y. Du, R. Liu, G. Linn and
K. Zhao, Org. Lett., 2006, 8, 5919; (i) Y. Amano and S. Nishiyama,
Tetrahedron Lett., 2006, 47, 6505; (j) Y. Kikugawa, A. Nagashima,
T. Sakamoto, E. Miyazawa and M. Shiiya, J. Org. Chem., 2003, 68,
6739.
4-Methoxy-2,5-d◦imethylacetanilide (3g). Yield (80%), white
solid; mp 163–165 C, 1H NMR (300 MHz, CDCl3) d 7.20 (br s,
1H, NH), 7.16 (s, 1H), 6.60 (s, 1H), 3.78 (s, 3H), 2.17 (s, 3H),
2.13 (s, 3H), 2.11 (s, 3H); 13C NMR (75 MHz, CDCl3) d 169.1,
155.8, 130.6, 130.4, 127.9, 124.6, 112.0, 55.5, 23.7, 18.0, 15.8; IR
(KBr) u 3296, 2927, 1653, 1592, 1534, 1467, 1400, 1210, 1030, 884,
719 cm-1; HRMS (EI) Calculated for C11H15NO2 (M+) 193.1103,
found 193.1099.
4-Methoxy-3,5-d◦imethylacetanilide (3h). Yield (75%), white
solid, mp 136–138 C, 1H NMR (300 MHz, CDCl3) d 8.07 (br s,
1H, NH), 7.10 (s, 2H), 3.64 (s, 3H), 2.20 (s, 6H), 2.11 (s, 3H); 13
C
NMR (75 MHz, CDCl3) d 169.2, 153.7, 133.4, 131.2 (2C), 121.0
(2C), 59.8, 24.1, 16.1 (2C); IR (KBr) u 3322, 2929, 1659, 1613,
1561, 1480, 1408, 1369, 1222, 1010, 862, 750 cm-1; HRMS (EI)
Calculated for C11H15NO2 (M+) 193.1103, found 193.1100.
4-Ethoxyacetanilide (3i). Yield (57%), white solid, mp 134–
136 ◦C, 1H NMR (300 MHz, CDCl3) d 7.36 (d, J = 9.0 Hz,
2H), 7.28 (br s, 1H, NH), 6.83 (d, J = 9.0 Hz, 2H), 4.00 (q, J =
6.9 Hz, 2H), 2.13 (s, 3H), 1.39 (t, J = 6.9 Hz, 3H); 13C NMR
(75 MHz, CDCl3) d 168.5, 155.9, 131.0, 122.1 (2C), 114.9 (2C),
63.8, 24.4, 14.9; IR (KBr) u 3366, 2927, 1665, 1605, 1512, 1374,
1280, 1124, 829, 745 cm-1; HRMS (EI) Calculated for C10H13NO2
(M+) 179.0946, found 179.0939.
4 For recent examples of hypervalent iodine compounds in C–C bond
formation: (a) Y. Gu and D. Wang, Tetrahedron Lett., 2010, 51, 2004;
(b) Y. Kita, K. Morimoto, M. Ito, C. Ogawa, A. Goto and T. Dohi,
J. Am. Chem. Soc., 2009, 131, 1668; (c) Y. Yang, C. Zheng and R. Fan,
Org. Lett., 2009, 11, 3156; (d) J. Liang, J. Chen, F. Du, X. Zeng, L.
4-◦Isopropoxyacetanilide (3j). Yield (52%), white solid, mp 130–
132 C, 1H NMR (300 MHz, CDCl3) d 7.36 (d, J = 9.0 Hz, 2H),
7.16 (br s, 1H, NH), 6.83 (d, J = 9.0 Hz, 2H), 4.48 (septet, J =
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