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The Journal of Organic Chemistry
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4,4,4-trifluoro-1-(4-fluorophenyl)butan-1-one (5d) 26 57.2 mg, 65% yield; Colorless oil; 1H NMR (400 MHz, CDCl3)
δ 8.10 – 7.91 (m, 2H), 7.15 (t, J = 8.6 Hz, 2H), 3.23 (dd, J = 9.9, 5.6 Hz, 2H), 2.68 – 2.48 (m, 2H); 13C {1H} NMR
(150 MHz, CDCl3) δ 194.7, 166.0 (d, J = 255.6 Hz), 132.6, 130.7 (d, J = 9.4 Hz), 127.1 (q, J = 274.5 Hz), 115.9 (d, J
= 22.0 Hz), 31.1, 28.3 (q, J = 29.8 Hz); 19F {1H} NMR (376 MHz, CDCl3) δ -66.49 (t, J = 10.8 Hz, 3F), -104.29 (ddd,
J = 13.2, 6.6, 4.3 Hz, 1F); MS (ESI) m/z 221.1 [M + H]+.
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1-(4-chlorophenyl)-4,4,4-trifluorobutan-1-one (5e) 86.9 mg, 92% yield; White solid; mp: 66.9-68.1 °C; H NMR
(400 MHz, CDCl3) δ 7.89 (d, J = 7.4 Hz, 2H), 7.43 (d, J = 7.4 Hz, 2H), 3.47 – 3.07 (m, 2H), 2.73 – 2.39 (m, 2H); 13C
{1H} NMR (150 MHz, CDCl3) δ 195.0, 140.1, 134.4, 129.4, 129.1, 127.0 (q, J = 274.5 Hz), 31.1, 28.2 (q, J = 29.8 Hz);
19F {1H} NMR (376 MHz, CDCl3) δ -66.58 (t, J = 10.8 Hz, 3F); MS (ESI) m/z 237.1 [M + H]+.
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1-(4-bromophenyl)-4,4,4trifluorobutan-1-one (5f) 106.8 mg, 95% yield; White solid; mp: 78.6-80.1 °C; H NMR
(400 MHz, CDCl3) δ 7.81 (d, J = 8.5 Hz, 2H), 7.60 (d, J = 8.5 Hz, 2H), 3.27 – 3.13 (m, 2H), 2.67 – 2.45 (m, 2H); 13C
{1H} NMR (150 MHz, CDCl3) δ 195.2, 134.8, 132.0, 129.4, 128.7, 127.0 (q, J = 273.0 Hz), 31.1, 28.2 (q, J = 29.8 Hz);
19F {1H} NMR (376 MHz, CDCl3) δ -66.44 (t, J = 10.8 Hz, 3F); MS (ESI) m/z 281.1 and 283.1 [M + H]+.
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(E)-1-(4,4-difluorobut-1-en-1-yl)-4-methoxybenzene (6a) 66.6 mg, 84% yield; Colorless oil; H NMR (400 MHz,
CDCl3) δ 7.33 (d, J = 8.6 Hz, 2H), 6.88 (d, J = 8.6 Hz, 2H), 6.51 (d, J = 15.9 Hz, 1H), 6.00 (dt, J = 15.7, 7.3 Hz, 1H),
5.86 (t, J = 4.4 Hz, 0.41H), 5.72 (t, J = 4.4 Hz, 0.16H), 3.82 (s, 3H), 2.84 – 2.64 (m, 2H); 13C {1H} NMR (150 MHz,
CDCl3) δ 159.3, 134.6, 129.5, 127.4, 117.2 (t, J = 238.5 Hz), 117.1 (t, J = 6.6 Hz), 114.0, 55.2, 38.0 (t, J = 21.9 Hz);
19F {1H} NMR (376 MHz, CDCl3) δ -115.53 (dtd, J = 56.7, 17.3, 2.4 Hz, 2F); HRMS (ESI): m/z [M + H]+ calcd for
C11H13F2O: 199.0929, found: 199.0935.
(E)-1-(4-fluorobut-1-en-1-yl)-4-methoxybenzene (6b) 18.0 mg, 25% yield; Colorless oil; 1H NMR (400 MHz, CDCl3)
δ 7.30 (d, J = 8.4 Hz, 2H), 6.85 (d, J = 8.4 Hz, 2H), 6.45 (d, J = 15.9 Hz, 1H), 6.15 – 5.98 (m, 1H), 4.53 (dt, J = 47.2,
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6.3 Hz, 2H), 3.79 (s, 3H), 2.59 (dq, J = 23.7, 6.5 Hz, 2H); C {1H} NMR (150 MHz, CDCl3) δ 158.9, 132.1, 129.9,
127.1, 126.2, 113.8, 83.1 (d, J = 167.7 Hz), 55.0, 33.9 (d, J = 20.5 Hz); 19F {1H} NMR (376 MHz, CDCl3) δ -217.02
(ttd, J = 47.4, 23.7, 2.7 Hz, 1F); HRMS (ESI): m/z [M + H]+ calcd for C11H14FO: 181.1023, found: 181.1022.
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(E)-1-methoxy-4-(5,5,5-trifluoropent-1-en-1-yl)benzene (6c) 17.5 mg, 19% yield; Pale yellow oil; H NMR (400
MHz, CDCl3) δ 7.29 (d, J = 8.5 Hz, 2H), 6.86 (d, J = 8.5 Hz, 2H), 6.40 (d, J = 15.8 Hz, 1H), 6.10 – 5.95 (m, 1H), 3.80
(s, 3H), 2.46 (dd, J = 15.4, 7.1 Hz, 2H), 2.33 – 2.15 (m, 2H); 13C {1H} NMR (150 MHz, CDCl3) δ 159.1, 131.0, 130.3,
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