No renderable structure data available
COC1=C(C(=CC=C1)OC)CBrChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 2-(bromomethyl)-1,3-dimethoxybenzene |
|---|---|
| IUPAC Name | — |
| CAS Number | 169610-52-0 |
| Database ID | 15556958 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
2-(bromomethyl)-1,3-dimethoxybenzene (CAS 169610-52-0) 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 15556958
Safety Notice
For professional research and industrial use only. Review the supplier safety data sheet before handling.
Synthesis data
10 reactions · 10 references
Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-3dbc25a88fa14bc8a4850d45b40f4954Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A stirred solution of 4.7 grams (0.020 mole) of 2,6-dimethoxyphenylmethyl bromide, 3.2 grams (0.020 mole) of ethyl piperidin-4-ylcarboxylate, and 23.5 grams (0.200 mole) of 50% potassium fluoride on Celite® filter aid in 100 mL of acetonitrile was heated at reflux for about 18 hours, after which the reaction mixture was cooled and filtered. The filtrate was concentrated under reduced pressure to a residue, which was subjected to column chromatography on silica gel, with mixtures of ethyl acetate in hexane as eluants. The product-containing fractions were combined and concentrated under reduced pressure to a residue. The residue was analyzed using thin layer chromatography, which indicated that the residue was impure. The residue was again subjected to column chromatography on silica gel, with mixtures of ethyl acetate in hexane and methanol in ethyl acetate as eluants. The product-containing fractions were combined and concentrated under reduced pressure, yielding about one gram of ethyl N-(2,6-dimethoxyphenylmethyl)piperidin-4-ylcarboxylate. The NMR spectrum was consistent with the proposed structure. was heated at reflux for about 18 hours after which the reaction mixture was cooled filtered The filtrate was concentrated under reduced pressure to a residue, which concentrated under reduced pressure to a residue concentrated under reduced pressure
Source ID: ord-9392da3f598a4280866734ccf0ec5d14Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A stirred solution of 4.7 grams (0.020 mole) of 2,6-dimethoxyphenylmethyl bromide, 3.2 grams (0.020 mole) of ethyl piperidin-4-ylcarboxylate, and 23.5 grams (0.200 mole) of 50% potassium fluoride on Celite® filter aid in 100 mL of acetonitrile was heated at reflux for about 18 hours, after which the reaction mixture was cooled and filtered. The filtrate was concentrated under reduced pressure to a residue, which was subjected to column chromatography on silica gel, with mixtures of ethyl acetate in hexane as eluants. The product-containing fractions were combined and concentrated under reduced pressure to a residue. The residue was analyzed using thin layer chromatography, which indicated that the residue was impure. The residue was again subjected to column chromatography on silica gel, with mixtures of ethyl acetate in hexane and methanol in ethyl acetate as eluants. The product-containing fractions were combined and concentrated under reduced pressure, yielding about one gram of ethyl N-(2,6-dimethoxyphenylmethyl)piperidin-4-ylcarboxylate. The NMR spectrum was consistent with the proposed structure. was heated at reflux for about 18 hours after which the reaction mixture was cooled filtered The filtrate was concentrated under reduced pressure to a residue, which concentrated under reduced pressure to a residue concentrated under reduced pressure
Source ID: ord-9392da3f598a4280866734ccf0ec5d14Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: After a mixture of 5.7 grams (0.034 mole) of 2,6-dimethoxyphenylmethanol in 40 mL of concentrated hydrobromic acid was stirred at ambient temperature for about one hour, the reaction mixture was taken up in diethyl ether. Solid sodium chloride was added to the mixture to obtain a phase separation. The organic layer was separated and concentrated under reduced pressure, yielding about 4.7 grams of 2,6-dimethoxyphenylmethyl bromide. This compound was used immediately in the next reaction. to obtain a phase separation The organic layer was separated concentrated under reduced pressure
Source ID: ord-7323ba6f5da0405a87601d1bbdbdb171Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-3dbc25a88fa14bc8a4850d45b40f4954Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A stirred solution of 4.7 grams (0.020 mole) of 2,6-dimethoxyphenylmethyl bromide, 3.2 grams (0.020 mole) of ethyl piperidin-4-ylcarboxylate, and 23.5 grams (0.200 mole) of 50% potassium fluoride on Celite® filter aid in 100 mL of acetonitrile was heated at reflux for about 18 hours, after which the reaction mixture was cooled and filtered. The filtrate was concentrated under reduced pressure to a residue, which was subjected to column chromatography on silica gel, with mixtures of ethyl acetate in hexane as eluants. The product-containing fractions were combined and concentrated under reduced pressure to a residue. The residue was analyzed using thin layer chromatography, which indicated that the residue was impure. The residue was again subjected to column chromatography on silica gel, with mixtures of ethyl acetate in hexane and methanol in ethyl acetate as eluants. The product-containing fractions were combined and concentrated under reduced pressure, yielding about one gram of ethyl N-(2,6-dimethoxyphenylmethyl)piperidin-4-ylcarboxylate. The NMR spectrum was consistent with the proposed structure. was heated at reflux for about 18 hours after which the reaction mixture was cooled filtered The filtrate was concentrated under reduced pressure to a residue, which concentrated under reduced pressure to a residue concentrated under reduced pressure
Source ID: ord-a139f7783188480298cdfc3e564ac19eConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: After a mixture of 5.7 grams (0.034 mole) of 2,6-dimethoxyphenylmethanol in 40 mL of concentrated hydrobromic acid was stirred at ambient temperature for about one hour, the reaction mixture was taken up in diethyl ether. Solid sodium chloride was added to the mixture to obtain a phase separation. The organic layer was separated and concentrated under reduced pressure, yielding about 4.7 grams of 2,6-dimethoxyphenylmethyl bromide. This compound was used immediately in the next reaction. to obtain a phase separation The organic layer was separated concentrated under reduced pressure
Source ID: ord-eb2f77d8a18b4dfeaac674b65fae4be0Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 76 mg of sodium hydride (80% in mineral oil) are added to a suspension of 400 mg of 6-hydroxy-3H-quinazolin-4-one in 20 ml of dry dimethylformamide. After stirring for 30 minutes at room temperature, 560 mg of 2,6-dimethoxybenzylbromide are added, and stirring is continued overnight. The solvent is distilled off in vacuo, and the residue partitioned between aqueous pH7-buffer solution and ethyl acetate. The organic phase is separated, dried over magnesium sulfate and evaporated in vacuo. Silica gel chromatography yields a minor amount of the N,O-bis-alkylated product followed by the pure title compound as colourless crystals. mp: 243-245°. stirring is continued overnight The solvent is distilled off in vacuo the residue partitioned between aqueous pH7-buffer solution and ethyl acetate The organic phase is separated dried over magnesium sulfate evaporated in vacuo Silica gel chromatography yields a minor amount of the N,O-bis-alkylated product
Source ID: ord-986f5b48d98b426ea1185b247b3c2d8dConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A stirred solution of 4.7 grams (0.020 mole) of 2,6-dimethoxyphenylmethyl bromide, 3.2 grams (0.020 mole) of ethyl piperidin-4-ylcarboxylate, and 23.5 grams (0.200 mole) of 50% potassium fluoride on Celite® filter aid in 100 mL of acetonitrile was heated at reflux for about 18 hours, after which the reaction mixture was cooled and filtered. The filtrate was concentrated under reduced pressure to a residue, which was subjected to column chromatography on silica gel, with mixtures of ethyl acetate in hexane as eluants. The product-containing fractions were combined and concentrated under reduced pressure to a residue. The residue was analyzed using thin layer chromatography, which indicated that the residue was impure. The residue was again subjected to column chromatography on silica gel, with mixtures of ethyl acetate in hexane and methanol in ethyl acetate as eluants. The product-containing fractions were combined and concentrated under reduced pressure, yielding about one gram of ethyl N-(2,6-dimethoxyphenylmethyl)piperidin-4-ylcarboxylate. The NMR spectrum was consistent with the proposed structure. was heated at reflux for about 18 hours after which the reaction mixture was cooled filtered The filtrate was concentrated under reduced pressure to a residue, which concentrated under reduced pressure to a residue concentrated under reduced pressure
Source ID: ord-9392da3f598a4280866734ccf0ec5d14Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: After a mixture of 5.7 grams (0.034 mole) of 2,6-dimethoxyphenylmethanol in 40 mL of concentrated hydrobromic acid was stirred at ambient temperature for about one hour, the reaction mixture was taken up in diethyl ether. Solid sodium chloride was added to the mixture to obtain a phase separation. The organic layer was separated and concentrated under reduced pressure, yielding about 4.7 grams of 2,6-dimethoxyphenylmethyl bromide. This compound was used immediately in the next reaction. to obtain a phase separation The organic layer was separated concentrated under reduced pressure
Source ID: ord-7323ba6f5da0405a87601d1bbdbdb171PubChem References
These sources are listed in the compound's public database record.
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