PAPER
Novel Conversion of Aryl Methyl Ethers into Mesylates
2027
4-Chlorophenyl Methanesulfonate (2c)
Anal. Calcd for C14H19NO4S: C, 56.54; H, 6.44; N, 4.71. Found: C,
56.32; H, 6.40; N, 4.50.
White solid; mp 70–72 °C (Lit.7 71 °C).
1H NMR (250 MHz, CDCl3): d = 7.40 (d, J = 8.75 Hz, 2 H), 7.30 (d,
J = 8.75 Hz, 2 H), 3.13 (s, 3 H).
13C NMR (62.9 MHz, CDCl3): d = 147.5, 133.0, 130.0, 123.4, 37.4.
4-(Benzoylamino)phenyl Methanesulfonate (2k)
White solid; mp 181–183 °C.
1H NMR (250 MHz, DMSO-d6): d = 10.42 (s, 1 H), 7.44 (d, J = 8
Hz, 2 H), 7.87 (d, J = 9 Hz, 2 H), 7.59–7.49 (m, 3 H), 7.33 (d, J = 9
Hz, 2 H), 3.35 (s, 3 H).
13C NMR (62.9 MHz, DMSO-d6): d = 166.1, 145.0, 138.6, 135.1,
132.1, 128.8, 128.1, 122.9, 121.9, 37.6.
4-Bromophenyl Methanesulfonate (2d)
White solid; mp 85–87 °C (Lit.7 83 °C).
1H NMR (250 MHz, CDCl3): d = 7.52 (d, J = 8.75 Hz, 2 H), 7.15 (d,
J = 8.75 Hz, 2 H), 3.19 (s, 3 H).
Anal. Calcd for C14H13NO4S: C, 57.72; H, 4.50; N, 4.81. Found: C,
57.55; H, 4.40; N, 4.61.
13C NMR (62.9 MHz, CDCl3): d = 148.1, 133.1, 123.8, 120.8, 37.4.
4-Fluorophenyl Methanesulfonate (2e)
4-Benzoylphenyl Methanesulfonate (2l)4c
White solid; mp 112–114 °C.
1H NMR (250 MHz, CDCl3): d = 7.87 (d, J = 8 Hz, 2 H), 7.77 (d,
J = 8 Hz, 2 H), 7.60 (m, 5 H), 3.20 (s, 3 H).
13C NMR (62.9 MHz, CDCl3): d = 195.1, 151.8, 137.0, 136.5,
Colorless oil.14
1H NMR (250 MHz, CDCl3): d = 7.25–6.91 (m, 4 H), 3.09 (s, 3 H).
13C NMR (62.9 MHz, CDCl3): d = 161.1 (d, JCF = 246.5 Hz), 145.0
(d, JCF = 3.1 Hz), 123.8 (d, JCF = 8.8 Hz), 116.6 (d, JCF = 27.6 Hz),
37.0.
132.8, 132.0, 129.9, 128.4, 121.8, 37.8.
3-Methylphenyl Methanesulfonate (2f)
2-(3-Methoxyphenyl)acetamide (3)
CAS No. 18463-71-3.
1H NMR (250 MHz, CDCl3): d = 7.40–7.25 (m, 2 H), 6.90–6.75 (m,
2 H), 5.70–5.30 (br, 2 H, NH2), 3.82 (s, 3 H), 3.58 (s, 2 H).
13C NMR (62.9 MHz, DMSO-d6): d = 172.6, 159.6, 138.4, 129.6,
121.8, 115.8, 115.2, 112.1.
Colorless oil.7
1H NMR (250 MHz, CDCl3): d = 7.23–6.93 (m, 4 H), 2.98 (s, 3 H),
2.25 (s, 3 H).
13C NMR (62.9 MHz, CDCl3): d = 149.4, 140.4, 129.6, 128.1,
122.5, 118.9, 37.0, 20.9.
2-Chlorophenyl Methanesulfonate (2g)
Colorless oil.7
Acknowledgment
1H NMR (250 MHz, CDCl3): d = 7.69–7.12 (m, 4 H), 3.22 (s, 3 H).
13C NMR (62.9 MHz, CDCl3): d = 145.2, 133.8, 128.3, 128.3,
The Institute for Advanced Studies in Basic Sciences (IASBS) is
thanked for supporting this work.
126.8, 124.3, 38.5.
2-Nitrophenyl Methanesulfonate (2h)
White solid; mp 94–96 °C.
References
(1) (a) Larock, R. C. Comprehensive Organic Transformations,
1st ed.; VCH: Weinheim, 1989. (b) Wagner, R. B.; Zokk, H.
D. Synthetic Organic Chemistry, Vol. 3; Horning, E. C., Ed.;
John Wiley & Sons: New York, 1955. (c) Sandler, S. R.;
Karo, W. Organic Functional Group Preparations, Vol. 1;
Academic: New York, 1983. (d) Kabalka, G. W.; Varma,
M.; Varma, R. S. J. Org. Chem. 1986, 51, 2386.
(e) Kazemi, F.; Massah, A. R.; Javaherian, M. Tetrahedron
2007, 63, 5083. (f) Kaboudin, B. Tetrahedron 1999, 55,
12865.
1H NMR (250 MHz, CDCl3): d = 8.04 (dd, J = 8.75, 1.5 Hz, 1 H),
7.71–7.42 (m, 3 H), 3.38 (s, 3 H).
13C NMR (62.9 MHz, CDCl3): d = 152.4, 141.0, 134.6, 127.7,
126.1, 125.3, 39.0.
Anal. Calcd for C7H7NO5S: C, 38.71; H, 3.25; N, 6.45. Found: C,
38.58; H, 3.15; N, 6.40.
Quinolin-6-yl Methanesulfonate (2i)
Yellow viscous oil.4c
(2) Cragg, P. J. A Practical Guide to Supramolecular
Chemistry; John Wiley & Sons: New York, 2005.
(3) (a) Giles, D. P.; Kerry, J. C.; Kozlik, A.; Palmer, B. H.;
Shutler, S. W.; Willis, R. J. EP 0,026,040, 1981; Chem.
Abstr. 1981, 95, 115059e. (b) Copping, L. G.; Kerry, J. C.;
Watkins, T. L.; Willis, R. J.; Palmer, B. H. US 4,344,893,
1982; Chem. Abstr. 1983, 98, 106973h. (c) Papas, S. P.;
Lam, Ch. W. J. Radiat. Curing 1980, 7, 2; Chem. Abstr.
1980, 92, 198859c.
1H NMR (250 MHz, CDCl3): d = 8.94 (dd, J = 4.25, 1.5 Hz, 1 H),
8.61 (d, J = 8.75 Hz, 2 H), 7.76 (d, J = 2.5 Hz, 1 H), 7.61 (dd,
J = 9.25, 2.5 Hz, 1 H), 7.45 (dd, J = 8.75, 4.25 Hz, 1 H), 3.22 (s, 3
H).
13C NMR (62.9 MHz, CDCl3): d = 151.0, 146.7, 136.0, 131.9,
128.4, 124.2, 122.0, 119.4, 37.6.
4-[(Cyclohexylcarbonyl)amino]phenyl Methanesulfonate (2j)
(4) (a) Percec, V.; Golding, G. M.; Smidrkal, J. J. Org. Chem.
2004, 69, 3447. (b) Buchwald, S. L.; Munday, R. H.;
Martinelli, J. R. J. Am. Chem. Soc. 2008, 130, 2754. (c) So,
C. M.; Lee, H. W.; Lau, C. P.; Kwong, F. Y. Org. Lett. 2009,
11, 317.
(5) (a) Tamura, T.; Kiyomine, A.; Nishizawa, Y.; Tanaka, M.;
Tagami, H.; Yoshihara, T.; Ogawa, M.; Muraoka, T.;
Kawase, J. JP 4,247,018, 1992; Chem. Abstr. 1993, 118,
45452. (b) Tamura, T.; Kiyomine, A.; Nishizawa, Y.;
Tanaka, M.; Tagami, H.; Yoshihara, T.; Ogawa, M.;
White solid; mp 170–172 °C.
1H NMR (250 MHz, CDCl3): d = 7.94 (d, J = 8.75 Hz, 2 H), 7.31 (d,
J = 8.75 Hz, 2 H), 6.46 (d, J = 8.25 Hz, 1 H), 3.93 (m, 1 H), 3.17 (s,
3 H), 2.01 (d, J = 9.5 Hz, 2 H), 1.72 (dd, J = 12.5, 9 Hz, 2 H), 1.30–
1.11 (m, 6 H).
13C NMR (62.9 MHz, CDCl3): d = 165.4, 160.2, 151.0, 134.1,
128.9, 122.0, 49.0, 37.7, 33.0, 25.4, 24.8.
Synthesis 2009, No. 12, 2025–2028 © Thieme Stuttgart · New York