Structure of 128495-45-4
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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CAS No. : | 128495-45-4 |
Formula : | C8H9FO2 |
M.W : | 156.15 |
SMILES Code : | OCC1=CC=C(F)C(OC)=C1 |
MDL No. : | MFCD00272133 |
InChI Key : | FZEDGSMVRLKUOQ-UHFFFAOYSA-N |
Pubchem ID : | 593590 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H317-H319 |
Precautionary Statements: | P280-P305+P351+P338 |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With manganese(IV) oxide; In dichloromethane; for 16h;Heating / reflux; | (4-FLUORO-3-METHOXYPHENYL) METHANOL (5. 00G, 0. 03mol) and manganese dioxide (33.4g, 0. 38MOL) were stirred in DICHLOROMETHANE (100ml) under an atmosphere of nitrogen, at gentle reflux for 16 hours. The cooled reaction mixture was then filtered through arbacel and concentrated in vacuo to give the title compound as a white solid (4.18g, 0. 027MOL, 85%). 1H NMR (CDCI3, 400MHZ) 8 : 3.96 (s, 3H), 7.23 (d, 1H), 7.43 (m, 1 H), 7.50 (d, 1 H) 9.91 (s, 1H). Mpt: 61-63C. Analysis found C, 62.18 ; H, 4.54%. C8H7FO2 requires C, 62.34 ; H, 4.58%. |
85% | With manganese(IV) oxide; In dichloromethane; for 16h;Heating / reflux; | (4-Fluoro-3-methoxyphenyl) methanol (5.0Og, 0.03mol) and manganese dioxide (33.4g, 0.38mol) were stirred in dichloromethane (100ml) under an atmosphere of nitrogen, at gentle reflux for 16 hours. The • cooled reaction mixture was then filtered through arbacel and concentrated in vacuo to give the title compound as a white solid (4.18g, 0.027mol, 85%). 1H NMR (CDCI3, 400MHz) δ: 3.96 (s, 3H), 7.23 (d, 1 H), 7.43 (m, 1 H), 7.50 (d, 1 H) 9.91 (s, 1 H). Mpt: 61-630C. Analysis found C, 62.18; H, 4.54%. C8H7FO2 requires C, 62.34; H, 4.58%. |
81% | With chromium trioxide pyridine; In dichloromethane; at 20℃; for 0.5h; | To a solution of (4-fluoro-3-methoxyphenyl) methanol (1.56 g, 10 mmol) in dichloromethane (40 mL) was added chromium trioxide pyridine (4.31 g, 20 mmol). The mixture was stirred at room temperature for 30 min and filtered. The filtrate was poured onto a short silica gel column, and eluted with dichloromethane. The resulting solution was concentrated under vacuum to afford the title compound (1.25 g, 81 %). 1H NMR (CDCl3): δ 9.92 (1H, s), 7.52 (1H, dd, J = 2.0 Hz, 8.4 Hz), 7.47-7.43 (1H, m), 7.26-7.22 (1H, m), 3.96 (3H, s). |
81% | With pyridine; chromium(VI) oxide; In dichloromethane; at 20℃; for 0.5h; | To a solution of (4-fluoro-3-methoxyphenyl) methanol (1.56 g, 10 mmol) in dichloromethane (40 mL) was added chromium trioxide pyridine (4.31 g, 20 mmol). The mixture was stirred at room temperature for 30 min and filtered. The filtrate was poured onto a short silica gel column, and eluted with dichloromethane. The resulting solution was concentrated under vacuum to afford the title compound (1.25 g, 81 %). 1H NMR (CDCl3): δ9.92 (1H, s), 7.52 (1H, dd, J=2.0 Hz, 8.4 Hz), 7.47-7.43 (1H, m), 7.26-7.22 (1H, m), 3.96 (3H, s). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide; sodium tetrahydroborate; In methanol; water; for 1h; | Preparation 44; To a solution of 4-fluoro-3-methoxybenzaldehyde (5 g) in methanol (25 ml) was added dropwise sodium borohydride (368 mg) in 0.1N sodium hydroxide aqueous solution (5 ml) in water bath and the whole was stirred for 1 hour. After the mixture was evaporated under reduced pressure, ethyl acetate and water were added thereto. The organic layer was separated and the water layer was further extracted with ethyl acetate. The combined organic layer was dried over magnesium sulfate and concentrated in vacuo to give 4-fluoro-3-methoxybenzyl-alcohol (5.22 g) as an oil. IR (Neat): 1610, 1516, 1462, 1417, 1315, 1277, 1149, 1115, 1032 cm-1 NMR (CDCl3, δ): 1.75 (1H, br s), 3.90 (3H, s), 4.64 (2H, s), 6.70-7.20 (3H, m) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With N-Bromosuccinimide; In acetonitrile; at 20℃; for 18h; | Preparation 33(2-Bromo-4-fluoro-5-methoxy-phenyl)-methanolTo a solution of (4-fluoro-3-methoxy-phenyl)-methanol (10.0g, 64.04mmol) in MeCN (160ml_) was added a solution of NBS (1 1 .4g, 64.04mmol) in MeCN (50ml_) and the resulting mixture was stirred at room temperature for 18 hours. The reaction mixture was concentrated in vacuo and the residue was suspended in diethyl ether (200ml_). Solid material was removed by filtration and washed with further diethyl ether. The filtrate was washed with water (200ml_) and brine (100mL), dried over MgS04 and concentrated in vacuo to give the title compound as a white solid (14.4g) in a 96% yield.1H NMR (400 MHz, CDCI3) δ ppm 1 .94 (t, 1 H), 3.90 (s, 3H), 4.70 (d, 2H), 7.14 (d, 1 H), 7.27 (d, 1 H). |
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