No renderable structure data available
FC1=CC=C(CO)C=C1OCChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 4-FLUORO-3-METHOXYBENZYL ALCOHOL |
|---|---|
| IUPAC Name | — |
| CAS Number | 128495-45-4 |
| Database ID | 593590 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
4-FLUORO-3-METHOXYBENZYL ALCOHOL (CAS 128495-45-4) product identity, structure identifiers and related reaction data for chemical intermediate research and sourcing review.
Potential Applications
For professional research and industrial use only
Database ID 593590
Safety Notice
For professional research and industrial use only. Review the supplier safety data sheet before handling.
Synthesis data
12 reactions · 12 references
Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-8e44ae9fe1684f6e9bb8a075c57a5189Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of (4-fluoro-3-methoxy-phenyl)-methanol (10.0 g, 64.04 mmol) in MeCN (160 mL) was added a solution of NBS (11.4 g, 64.04 mmol) in MeCN (50 mL) 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 (200 mL). Solid material was removed by filtration and washed with further diethyl ether. The filtrate was washed with water (200 mL) and brine (100 mL), dried over MgSO4 and concentrated in vacuo to give the title compound as a white solid (14.4 g) in a 96% yield. The reaction mixture was concentrated in vacuo Solid material was removed by filtration washed with further diethyl ether The filtrate was washed with water (200 mL) and brine (100 mL) dried over MgSO4 concentrated in vacuo
Source ID: ord-95ed5d69fb934c2cab84465c34bbcf83Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: (4-Fluoro-3-methoxyphenyl)methanol (5.00 g, 0.03 mol) and manganese dioxide (33.4 g, 0.38 mol) were stirred in dichloromethane (100 ml) 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 (4.18 g, 0.027 mol, 85%). 1H NMR (CDCl3, 400 MHz) δ: 3.96 (s, 3H), 7.23 (d, 1H), 7.43 (m, 1H), 7.50 (d, 1H) 9.91 (s, 1H). Mpt: 61-63° C. Analysis found C, 62.18; H, 4.54%. C8H7FO2 requires C, 62.34; H, 4.58%. at gentle reflux for 16 hours The cooled reaction mixture was then filtered through arbacel concentrated in vacuo
Source ID: ord-9e6234b5aebf4c60b818091ed9b7f852Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of (4-fluoro-3-methoxy-phenyl)-methanol (10.0 g, 64.04 mmol) in MeCN (160 mL) was added a solution of NBS (11.4 g, 64.04 mmol) in MeCN (50 mL) 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 (200 mL). Solid material was removed by filtration and washed with further diethyl ether. The filtrate was washed with water (200 mL) and brine (100 mL), dried over MgSO4 and concentrated in vacuo to give the title compound as a white solid (14.4 g) in a 96% yield. The reaction mixture was concentrated in vacuo Solid material was removed by filtration washed with further diethyl ether The filtrate was washed with water (200 mL) and brine (100 mL) dried over MgSO4 concentrated in vacuo
Source ID: ord-95ed5d69fb934c2cab84465c34bbcf83Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of (4-fluoro-3-methoxy-phenyl)-methanol (10.0 g, 64.04 mmol) in MeCN (160 mL) was added a solution of NBS (11.4 g, 64.04 mmol) in MeCN (50 mL) 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 (200 mL). Solid material was removed by filtration and washed with further diethyl ether. The filtrate was washed with water (200 mL) and brine (100 mL), dried over MgSO4 and concentrated in vacuo to give the title compound as a white solid (14.4 g) in a 96% yield. The reaction mixture was concentrated in vacuo Solid material was removed by filtration washed with further diethyl ether The filtrate was washed with water (200 mL) and brine (100 mL) dried over MgSO4 concentrated in vacuo
Source ID: ord-95ed5d69fb934c2cab84465c34bbcf83Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-8e44ae9fe1684f6e9bb8a075c57a5189Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of (4-fluoro-3-methoxyphenyl)methanol (Claudi, et al., J. Med. Chem. 1990, 33(9):2408) (0.90 g, 5.76 mmol) in anhydrous dichloromethane (10 mL) was added thionyl chloride (0.84 mL, 12 mmol) and anhydrous N,N-dimethylformamide (2 drops). The reaction mixture was stirred at ambient temperature for 16 h and concentrated in vacuo to afford 4-(chloromethyl)-1-fluoro-2-methoxybenzene (0.73 g, 72%) as a brown oil: 1H NMR (300 MHz, CDCl3) δ 7.05-6.86 (m, 3H), 4.53 (s, 2H), 3.88 (s, 3H). concentrated in vacuo
Source ID: ord-6040d227eb1745c8ad0c267a85c6e7e9Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: (4-Fluoro-3-methoxyphenyl) methanol (5.00 g, 0.03 mol) and manganese dioxide (33.4 g, 0.38 mol) were stirred in dichloromethane (100 ml) 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 (4.18 g, 0.027 mol, 85%). 1H NMR (CDCl3, 400 MHz) δ: 3.96 (s, 3H), 7.23 (d, 1H), 7.43 (m, 1H), 7.50 (d, 1H) 9.91 (s, 1H). Mpt: 61-63° C. Analysis found C, 62.18; H, 4.54%. C8H7FO2 requires C, 62.34; H, 4.58%. at gentle reflux for 16 hours The cooled reaction mixture was then filtered through arbacel concentrated in vacuo
Source ID: ord-7a6fdbe87b644480ad64881e2a07d946Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: (4-Fluoro-3-methoxyphenyl)methanol (5.00 g, 0.03 mol) and manganese dioxide (33.4 g, 0.38 mol) were stirred in dichloromethane (100 ml) 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 (4.18 g, 0.027 mol, 85%). 1H NMR (CDCl3, 400 MHz) δ: 3.96 (s, 3H), 7.23 (d, 1H), 7.43 (m, 1H), 7.50 (d, 1H), 9.91 (s, 1H). Mpt: 61-63° C. Analysis found C, 62.18; H, 4.54%. C8H7FO2 requires C, 62.34; H, 4.58%. at gentle reflux for 16 hours The cooled reaction mixture was then filtered through arbacel concentrated in vacuo
Source ID: ord-d97d539b205a4da8b70adbf065de16e3Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: After dissolving 9.17 g of (4-fluoro-3-methoxyphenyl)methanol [CAS No. 128495-45-4] in 100 ml of DMT, 5g of imidazole and 17g of t-butyl -chlorodiphenylsilane were added and the mixture was stirred overnight at room temperature. Next, 1N hydrochloric acid was added to the reaction mixture, and extraction was performed with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate. The desiccating agent was filtered off and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate-heptane) to give t-butyl-(4-fluoro-3-methoxybenzyloxy)diphenylsilane as an oil. The organic layer was dried over anhydrous magnesium sulfate The desiccating agent was filtered off the filtrate was concentrated under reduced pressure The residue was purified by silica gel column chromatography (ethyl acetate-heptane)
Source ID: ord-3571530c93cb4b3ca4c1cc3c21131d56Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of (4-fluoro-3-methoxy-phenyl)-methanol (10.0 g, 64.04 mmol) in MeCN (160 mL) was added a solution of NBS (11.4 g, 64.04 mmol) in MeCN (50 mL) 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 (200 mL). Solid material was removed by filtration and washed with further diethyl ether. The filtrate was washed with water (200 mL) and brine (100 mL), dried over MgSO4 and concentrated in vacuo to give the title compound as a white solid (14.4 g) in a 96% yield. The reaction mixture was concentrated in vacuo Solid material was removed by filtration washed with further diethyl ether The filtrate was washed with water (200 mL) and brine (100 mL) dried over MgSO4 concentrated in vacuo
Source ID: ord-e4b63e219e9f4ffbabf8404c47784842Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of (4-fluoro-3-methoxyphenyl)methanol (Claudi, et al., J. Med. Chem. 1990, 33(9):2408) (0.90 g, 5.76 mmol) in anhydrous dichloromethane (10 mL) was added thionyl chloride (0.84 mL, 12 mmol) and anhydrous N,N-dimethylformamide (2 drops). The reaction mixture was stirred at ambient temperature for 16 h and concentrated in vacuo to afford 4-(chloromethyl)-1-fluoro-2-methoxybenzene (0.73 g, 72%) as a brown oil: 1H NMR (300 MHz, CDCl3) δ 7.05-6.86 (m, 3H), 4.53 (s, 2H), 3.88 (s, 3H). concentrated in vacuo
Source ID: ord-569e166e9225445998894117fee5b247PubChem References
These sources are listed in the compound's public database record.
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