Organic & Biomolecular Chemistry
Paper
263.1432; Anal. Calcd for C19H18O: C, 86.99; H, 6.92. Found: colorless oil66 (45 mg, 93%); 1H-NMR (300 MHz, CDCl3): δ 7.07
C, 87.02; H, 6.67.
(s, 4H), 6.80 (s, 2H), 3.81 (s, 2H), 3.69 (s, 3H), 2.32 (s, 3H), 2.24
(p-Anisyl)(2,3-dihydro-benzo[1,4]dioxin-6-yl)methane (3m). (s, 6H); 13C-NMR (125 MHz, CDCl3): δ 155.2, 138.4, 136.6,
From 0.2 mmol (105 mg) of 1m (0.02 mmol (5 mg) I2, r.t. = 135.4, 130.6, 129.1, 129.1, 128.7, 59.7, 40.9, 21.0, 16.1;
30 min, 85 °C); preparative chromatography (SiO2, hexane/ IR(neat): 2997, 2920, 2859, 2510, 1484, 1440, 1376, 1310, 1223,
CH2Cl2 = 1/1); colorless oil (30 mg, 59%); H-NMR (300 MHz, 1143, 1016, 877, 811, 761, 644 cm−1; MS (ESI): 241.2 (M + H)+.
1
CDCl3): δ 7.10 (d, J = 8.6 Hz, 2H), 6.83 (d, J = 8.6 Hz, 2H), 6.78
(p-Anisyl)(4-methoxy-3,5-dimethylphenyl)methane (3r).
(d, J = 8.1 Hz, 1H), 6.70–6.62 (m, 2H), 4.22 (s, 4H), 3.82 (s, 2H), From 0.2 mmol (105 mg) of 1r (0.02 mmol (5 mg) I2, r.t. =
3.79 (s, 3H); 13C-NMR (75 MHz, CDCl3): δ 157.9, 143.3, 141.7, 30 min, 85 °C); preparative chromatography (SiO2, hexane/
1
135.0, 133.4, 129.7, 121.6, 117.4, 117.1, 113.9, 64.4, 64.3, 55.2, CH2Cl2 = 1/1); colorless oil (35 mg, 68%); H-NMR (300 MHz,
40.3; IR(neat): 3030, 2930, 2835, 1610, 1587, 1504, 1461, 1435, CDCl3): δ 7.11 (d, J = 8.6 Hz, 2H), 6.87–6.80 (m, 4H), 3.81 (s,
1286, 1244, 1204, 1177, 1125, 1067, 1035, 919, 886, 809, 767, 2H), 3.79 (s, 3H), 3.70 (s, 3H), 2.25 (s, 6H); 13C-NMR (75 MHz,
740 cm−1; MS (ESI): 256.1 (M)+; HRMS: calcd for C16H16O3: CDCl3): δ 157.9, 155.2, 136.8, 133.6, 130.6, 129.8, 129.1, 113.8,
256.1099; found: 256.1102; Anal. Calcd for C16H16O3: C, 74.98; 59.7, 55.2, 40.4, 16.1; IR(neat): 2995, 2932, 2834, 1611, 1508,
H, 6.29. Found: C, 74.96; H, 6.43.
1484, 1298, 1244, 1223, 1177, 1142, 1106, 1016, 819, 766,
4-(3,4-Dimethylbenzyl)-2-((p-anisyl)(3,4-dimethylphenyl)methyl)- 635 cm−1; MS (ESI): 256.1 (M)+; HRMS: calcd for C17H20O2:
1-methoxybenzene (3nn). From 0.2 mmol (93 mg) of 1n 256.1463; found: 256.1464; Anal. Calcd for C17H20O2: C, 79.65;
(0.02 mmol (5 mg) I2, r.t. = 30 min, 85 °C); preparative H, 7.86. Found: C, 79.53; H, 8.05.
chromatography (SiO2, hexane/CH2Cl2 = 6/4); colorless oil
(14 mg, 24%); 1H-NMR (300 MHz, CDCl3): δ 7.06–6.94 (m, 5H), 0.2 mmol (93 mg) of 1s (0.02 mmol (5 mg) I2, r.t. = 30 min,
6.91–6.75 (m, 8H), 5.82 (s, 1H), 3.80 (s, 3H), 3.79 (s, 2H), 3.71 85 °C); preparative chromatography (SiO2, hexane/CH2Cl2
(2-Methoxy-5-methylphenyl)(p-tolyl)methane (3s). From
=
(s, 3H), 2.24 (s, 3H), 2.24 (s, 3H), 2.22 (s, 3H), 2.20 (s, 3H); 1/1); colorless oil (30 mg, 66%); 1H-NMR (300 MHz, CDCl3):
13C-NMR (125 MHz, CDCl3): δ 157.6, 155.4, 141.6, 139.1, 136.4, δ 7.10 (d, J = 8.3 Hz, 2H), 7.06 (d, J = 8.3 Hz, 2H), 6.96 (dd, J =
136.3, 136.0, 133.9, 133.8, 132.9, 132.9, 131.0, 130.7, 130.3, 8.2 Hz, J = 1.8 Hz, 1H), 6.87 (d, J = 1.8 Hz, 1H), 6.75 (d, J =
130.0, 129.5, 129.2, 127.4, 126.7, 126.0, 113.3, 110.8, 55.8, 55.2, 8.2 Hz, 1H), 3.89 (s, 2H), 3.78 (s, 3H), 2.30 (s, 3H), 2.22 (s, 3H);
48.1, 40.6, 19.8, 19.7, 19.4, 19.3; IR(neat): 3001, 2932, 2834, 13C-NMR (75 MHz, CDCl3): δ 155.3, 138.1, 135.1, 131.0, 129.6,
1609, 1509, 1498, 1456, 1245, 1177, 1109, 1035, 808 cm−1; MS 129.6, 128.9, 128.8, 127.5, 110.5, 55.5, 35.3, 21.0, 20.5;
(ESI): 450.3 (M)+; HRMS: calcd for C32H34O2: 450.2559; found: IR(neat): 3001, 2921, 2833, 1611, 1500, 1460, 1252, 1182, 1122,
450.2545; Anal. Calcd for C32H34O2: C, 85.29; H, 7.61. Found: 1036, 805, 767, 720 cm−1; MS (ESI): 225.1 (M − H)+; HRMS:
C, 85.36; H, 7.23.
calcd for C16H17O: 225.1279; found: 225.1282; Anal. Calcd for
(3-Bromo-4-methoxyphenyl)(phenyl)methane
(3o). From C16H18O: C, 84.91; H, 8.02. Found: C, 84.90; H, 8.25.
0.2 mmol (114 mg) of 1o (0.02 mmol (5 mg) I2, r.t. = 6 h,
85 °C); preparative chromatography (SiO2, hexane/CH2Cl2
6/4); colorless oil (50 mg, 91%); H-NMR (300 MHz, CDCl3): δ 85 °C); preparative chromatography (SiO2, hexane/CH2Cl2
(p-Anisyl)(4-methoxy-2,3-dimethylphenyl)methane (3t). From
0.2 mmol (105 mg) of 1t (0.02 mmol (5 mg) I2, r.t. = 1.5 h,
=
1
=
7.38 (d, J = 2.0 Hz, 1H), 7.35–7.27 (m, 2H), 7.25–7.20 (m, 1H), 1/1); white solid (32 mg, 62%); mp: 66.9–67.6 °C; 1H-NMR
7.20–7.14 (m, 2H), 7.08 (dd, J = 8.4 Hz, J = 2.0 Hz, 1H), 6.82 (d, (300 MHz, CDCl3): δ 7.01 (d, J = 8.5 Hz, 2H), 6.92 (d, J = 8.3 Hz,
J = 8.4 Hz, 1H), 3.91 (s, 2H), 3.87 (s, 3H); 13C-NMR (75 MHz, 1H), 6.80 (d, J = 8.5 Hz, 2H), 6.67 (d, J = 8.3 Hz, 1H), 3.90 (s,
CDCl3): δ 154.3, 140.7, 134.8, 133.6, 128.8, 128.5, 126.2, 112.0, 2H), 3.80 (s, 3H), 3.77 (s, 3H), 2.16 (s, 3H), 2.12 (s, 3H);
111.6, 56.3, 40.7; IR(neat): 3060, 3026, 2936, 2904, 2835, 1603, 13C-NMR (75 MHz, CDCl3): δ 157.7, 156.1, 136.4, 133.3, 131.4,
1493, 1453, 1439, 1403, 1281, 1255, 1182, 1055, 1022, 797, 770, 129.4, 127.7, 125.4, 113.7, 107.6, 55.5, 55.2, 38.8, 15.8, 12.0;
728, 698, 671, 619 cm−1; Anal. Calcd for C14H13BrO: C, 60.67; IR(KBr): 3001, 2909, 2832, 1611, 1585, 1510, 1460, 1306, 1254,
H, 4.73. Found: C, 60.77; H, 4.65.
1172, 1102, 1064, 1034, 806, 752 cm−1; MS (ESI): 256.1 (M)+;
(3-Bromo-4-methoxyphenyl)(p-tolyl)methane
(3p). From HRMS: calcd for C17H20O2: 256.1463; found: 256.1461; Anal.
0.2 mmol (119 mg) of 1p (0.02 mmol (5 mg) I2, r.t. = 1.5 h, Calcd for C17H20O2: C, 79.65; H, 7.86. Found: C, 79.77; H, 7.81.
85 °C); preparative chromatography (SiO2, hexane/CH2Cl2 (4,5-Dimethoxy-2-methylphenyl)(p-tolyl)methane (3u). From
=
6/4); white solid (50 mg, 86%); mp: 37.7–38.4 °C; 1H-NMR 0.2 mmol (105 mg) of 1u (0.02 mmol (5 mg) I2, r.t. = 1 h,
(300 MHz, CDCl3): δ 7.37 (d, J = 2.1 Hz, 1H), 7.14–7.03 (m, 5H), 85 °C); preparative chromatography (SiO2, CH2Cl2) white solid
6.81 (d, J = 8.4 Hz, 1H), 3.86 (s, 5H), 2.33 (s, 3H); 13C-NMR (43 mg, 83%); mp: 70.5–72.4 °C; 1H-NMR (300 MHz, CDCl3):
(75 MHz, CDCl3): δ 154.2, 137.7, 135.7, 135.2, 133.6, 129.2, δ 7.07 (d, J = 7.9 Hz, 2H), 6.99 (d, J = 7.9 Hz, 2H), 6.69 (s, 1H),
128.7, 128.7, 112.0, 111.6, 56.3, 40.2, 21.0; IR(KBr): 2914, 2849, 6.65 (s, 1H), 3.88 (s, 2H), 3.85 (s, 3H), 3.80 (s, 3H), 2.30 (s, 3H),
1609, 1494, 1439, 1259, 1187, 1051, 1020, 893, 796, 748, 670, 2.18 (s, 3H); 13C-NMR (75 MHz, CDCl3): δ 147.2, 146.9, 137.6,
605 cm−1; Anal. Calcd for C15H15BrO: C, 61.87; H, 5.19. Found: 135.3, 130.9, 129.0, 128.5, 128.3, 56.0, 55.9, 38.5, 20.9, 19.1;
C, 62.12; H, 5.35.
IR(KBr): 2955, 2920, 1607, 1514, 1462, 1341, 1225, 1200, 1161,
(4-Methoxy-3,5-dimethylphenyl)(p-tolyl)methane (3q). From 1099, 997, 867, 841, 800, 755 cm−1; MS (ESI): 256.1 (M)+;
0.2 mmol (99 mg) of 1q (0.02 mmol (5 mg) I2, r.t. = 3 h, 85 °C); HRMS: calcd for C17H20O2: 256.1463; found: 256.1463; Anal.
preparative chromatography (SiO2, hexane/CH2Cl2
=
6/4); Calcd for C17H20O2: C, 79.65; H, 7.86. Found: C, 79.65; H, 7.54.
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Org. Biomol. Chem., 2013, 11, 1978–1999 | 1995