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Organic & Biomolecular Chemistry
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Hz, 1H), 7.14–7.21 (m, 1H), 7.22–7.25 (m, 1H), 7.84 (q, J = 4.5 6-Chloro-3-vinylisobenzofuran-1(3H)-one (4c)
ARTICLE
Hz, 1H); 13C{1H} NMR (CDCl3, 125 MHz) δ 11.3, 105.6, 106.3 (d, The procedure to prepare 4 was followed. Starting with 1c (19.7
DOI: 10.1039/D0OB00303D
2JC-F = 24.8 Hz), 117.7 (d, 2JC-F = 24.3 Hz), 120.6, 127.7 (d, 3JC-F
=
mg, 0.10 mmol), HCl(aq) (1 N, 50 µL, 50 µmol), and White cat (5.0
10.3 Hz), 142.0 (d, 3JC-F = 11.3 Hz), 145.5, 166.7 (d, 1JC-F = 253.3 mg, 10 µmol) in DMSO (1 mL), compound 4c (10.9 mg, 0.056
Hz), 165.9. The NMR spectroscopic data were consistent with mmol, 56%) was produced after column chromatography (SiO2,
the literature.81
ethyl acetate/hexanes, 1:20; Rf 0.45) as a colourless liquid. 1H
NMR (CDCl3, 500 MHz) δ 5.39 (m, 1H), 5.55 (m, 1H), 5.76–5.83
(m, 2H), 7.39 (s, 1H), 7.33 (d, J = 8.1 Hz, 1H), 7.61 (dd, J = 1.4 Hz,
5-Fluoro-3-vinylisobenzofuran-1(3H)-one (4a)
The procedure to prepare 4 was followed. Starting with 1a (19.6 8.0 Hz, 1H), 7.84 (d, J = 8.1 Hz, 1H); 13C{1H} NMR (CDCl3, 125
mg, 0.10 mmol), HCl(aq) (1 N, 50 µL, 50 µmol), and White cat (5.0 MHz) δ 29.6, 81.8,120.3, 123.7, 125.6, 132.8, 134.4, 135.8,
mg, 10 µmol) in DMSO (1 mL), compound 4a (11.5 mg, 0.065 146.6, 168.6; HRMS (ESI) calcd for [M + H]+ (C10H8ClO2)
mmol, 65%) was produced after column chromatography (SiO2, 195.0213, found 195.0205.
ethyl acetate/hexanes, 1:20; Rf 0.45) as a colourless liquid. 1H
NMR (CDCl3, 300 MHz) δ 5.39 (d, J = 15.3 Hz, 1H), 5.62 (d, J = (Z)-6-Bromo-3-ethylideneisobenzofuran-1(3H)-one (3d). The
20.0 Hz, 1H), 5.75–5.87 (m, 2H), 7.39 (s, 1H), 7.18 (dd, J = 7.5 Hz, procedure to prepare 3 was followed. Starting with 1d (24.0 mg,
J = 8.1 Hz, 1H), 7.80 (d, J = 8.1 Hz, 1H); 13C{1H} NMR (CDCl3, 75 0.10 mmol), NaOH(aq) (1 N, 50 µL, 50 µmol), and White cat (2.5
MHz) δ 81.3, 109.8 (d, 2JC-F = 24.2 Hz), 117.7 (d, 2JC-F = 23.9 Hz), mg, 5 µmol) in DMSO (1 mL), and compound 3d (15.5 mg, 0.065
120.5, 121.7, 128.1 (d, 3JC-F = 10.1 Hz), 132.7, 151.3 (d, 3JC-F = 9.6 mmol, 65%) was produced after column chromatography (SiO2,
Hz), 166.6 (d, 1JC-F = 255.0 Hz), 169.0; HRMS (ESI) calcd for [M + ethyl acetate/hexanes, 1:20; Rf 0.50) as a colourless liquid. 1H
H] + (C10H8FO2) 179.0508, found 179.0502.
NMR (CDCl3, 300 MHz) δ 1.98 (d, J = 7.2 Hz, 3H), 5.63 (q, J = 7.2
Hz, 1H), 7.46 (d, J = 8.1 Hz, 1H), 7.73 (dd, J = 1.8 Hz, J = 8.4 Hz,
1H), 7.99 (d, J = 1.5 Hz, 1H); 13C{1H} NMR (CDCl3, 75 MHz) δ 11.3,
(Z)-5-Chloro-3-ethylideneisobenzofuran-1(3H)-one (3b)
The procedure to prepare 3 was followed. Starting with 1b (19.7 105.3, 120.8, 120.9, 123.1, 126.1, 128.1, 137.3, 137.4, 138.1,
mg, 0.10 mmol), NaOH(aq) (1 N, 50 µL, 50 µmol), and White cat 145.7, 165.5. The NMR spectroscopic data were consistent with
(2.5 mg, 5 µmol) in DMSO (1 mL), compound 3b (12.6 mg, 0.065 the literature.82
mmol, 65%) as a colourless liquid was produced after column
chromatography (SiO2, ethyl acetate/hexanes, 1:20; Rf 0.50). 1H 6-Bromo-3-vinylisobenzofuran-1(3H)-one (4d)
NMR (CDCl3, 300 MHz) δ 1.99 (d, J = 7.3 Hz, 3H), 5.63 (q, J = 7.2 The procedure to prepare 4 was followed. Starting with 1d (24.0
Hz, 1H), 7.43 (d, J = 7.2 Hz, 1H), 7.58 (s, 1H), 7.78 (d, J = 8.1 Hz, mg, 0.10 mmol), HCl(aq) (1 N, 50 µL, 50 µmol), and White cat (5.0
1H); 13C{1H} NMR (CDCl3, 125 MHz) δ 11.3, 105.7, 119.7, 122.8, mg, 10 µmol) in DMSO (1 mL), compound 4d (20.3 mg, 0.085
126.5, 129.9, 140.9, 141.0, 145.3, 166.0. The NMR spectroscopic mmol, 85%) was produced after column chromatography (SiO2,
data were consistent with the literature.81
ethyl acetate/hexanes, 1:20; Rf 0.45) as a colourless liquid. 1H
NMR (CDCl3, 500 MHz) δ 5.40 (d, J = 9.2 Hz, 1H), 5.60 (d, J = 16.5
Hz, 1H), 5.75–5.83 (m, 2H), 7.27 (d, J = 8.1 Hz, 1H), 7.76 (dd, J =
5-Chloro-3-vinylisobenzofuran-1(3H)-one (4b)
The procedure to prepare 4 was followed. Starting with 1b (19.7 1.7 Hz, J = 8.1 Hz, 1H), 8.01 (d, J = 1.7 Hz, 1H); 13C{1H} NMR
mg, 0.10 mmol), HCl(aq) (1 N, 50 µL, 50 µmol), and White cat (5.0 (CDCl3, 125 MHz) δ 81.8, 120.4, 123.4, 124.0, 127.7, 128.7,
mg, 10 µmol) in DMSO (1 mL), compound 4b (16.7 mg, 0.086 132.7, 137.2, 147.1, 168.5; HRMS (ESI) calcd for [M + H]+
mmol, 86%) was produced after column chromatography (SiO2, (C10H8BrO2) 238.9707, found 238.9690. The NMR spectroscopic
ethyl acetate/hexanes, 1:20; Rf 0.45) as a colourless liquid. 1H data were consistent with the literature.46
NMR (CDCl3, 300 MHz) δ 5.41 (m, 1H), 5.57 (m, 1H), 5.75–5.86
(m, 2H), 7.39 (s, 1H), 7.48 (dd, J = 1.2 Hz, J = 8.1 Hz, 1H), 7.80 (d, (Z)-3-Ethylidene-6-methoxyisobenzofuran-1(3H)-one (3e)
J = 8.1 Hz, 1H);13C{1H} NMR (CDCl3, 75 MHz) δ 81.4, 120.6, 122.9, The procedure to prepare 3 was followed. Starting with 1e (19.0
126.9, 128.0, 130.2, 132.7, 140.9, 150.1, 169.0; HRMS (ESI) calcd mg, 0.10 mmol), NaOH(aq) (1 N, 50 µL, 50 µmol), and White cat
for [M + H]+ (C10H8ClO2) 195.0213, found 195.0202.
(2.5 mg, 5 µmol) in DMSO (1 mL), compound 3e (13.5 mg, 0.071
mmol, 71%) as a colourless liquid was produced after column
chromatography (SiO2, ethyl acetate/hexanes, 1:20; Rf 0.50). 1H
(Z)-6-Chloro-3-ethylideneisobenzofuran-1(3H)-one (3c)
The procedure to prepare 3 was followed. Starting with 1c (19.7 NMR (CDCl3, 300 MHz) δ 1.96 (d, J = 7.2 Hz, 3H), 3.85 (s, 3H),
mg, 0.10 mmol), NaOH(aq) (1 N, 50 µL, 50 µmol), and White cat 5.46 (q, J = 7.2 Hz, 1H), 7.19–7.27 (m, 2H), 7.47 (d, J = 8.4 Hz,
(2.5 mg, 5 µmol) in DMSO (1 mL), compound 3c (5 mg, 0.026 1H); 13C{1H} NMR (CDCl3, 75 MHz) δ 11.1, 55.8, 102.4, 106.3,
mmol, 26%) was produced after column chromatography (SiO2, 120.7, 123.7, 125.8, 132.7, 146.1, 160.8, 167.2. The NMR
ethyl acetate/hexanes, 1:20; Rf 0.50) as a colourless liquid. 1H spectroscopic data were consistent with the literature.83
NMR (CDCl3, 300 MHz) δ 2.03 (d, J = 7.2 Hz, 3H), 5.63 (q, J = 7.5 6-Methoxy-3-vinylisobenzofuran-1(3H)-one (4e)
Hz, 1H), 7.27 (m, 2H), 7.87 (d, J = 0.6 Hz, 1H); 13C{1H} NMR The procedure to prepare 4 was followed. Starting with 1e (19.0
(CDCl3, 75 MHz) δ 11.3, 105.2, 120.7, 125.1, 125.9, 134.6, 135.4, mg, 0.10 mmol), HCl(aq) (1 N, 50 µL, 50 µmol), and White cat (5.0
137.7, 145.6, 165.6; HRMS (ESI) calcd for [M+H]+ (C10H8ClO2) mg, 10 µmol) in DMSO (1 mL), compound 4e (7.9 mg, 0.042
195.0213, found 195.0204.
mmol, 42%) was produced after column chromatography (SiO2,
ethyl acetate/hexanes, 1:20; Rf 0.45) as a colourless liquid. 1H
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