No renderable structure data available
C1CCCC(CC1)BrChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | bromocycloheptane |
|---|---|
| IUPAC Name | — |
| CAS Number | 2404-35-5 |
| Database ID | 16992 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
bromocycloheptane (CAS 2404-35-5) 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 16992
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-f9f038eb966a4a8aaa846e66f1920be2Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-5de9a74d1eb440119425f051c43b429aConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-5a37b3e1d7034e90ab77b48863315902Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-60bee19a6cda4ed29ccc9a53a58fafe8Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-408e12cc711940c0b0a0f67ad75ec48aConditions: temp:-70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of magnesium metal (4.81 g, 200 mmol) and dry tetrahydrofuran (10 mL) under argon was treated with a solution of 1,2-dibromoethane (0.94 g, 5 mmol) in dry tetrahydrofuran (5 mL). The resulting reaction mixture was stirred for 10 min to activate the magnesium metal. The reaction mixture was then treated dropwise with a solution of cycloheptyl bromide (17.7 g, 100 mmol) in dry tetrahydrofuran (30 mL), one-fifth portion over a period of 5 min. The resulting reaction mixture was stirred for 5-10 min to initiate the exothermic reaction. The remaining portion of the cycloheptyl bromide solution was then added dropwise while controlling the inside temperature below 50° C. After complete addition, the solution was stirred for 1 h and then diluted with dry tetrahydrofuran (80 mL). In a separate reaction flask, a mixture of lithium chloride (8.48 g, 200 mmol, predried at 130° C. under high vacuum for 3 h) and copper(I) cyanide (8.96 g, 100 mmol) in dry tetrahydrofuran (110 mL) was stirred at 25° C. under argon for 10 min to obtain a clear solution. The reaction mixture was cooled to −70° C. and then slowly treated with the freshly prepared cycloheptylmagnesium bromide. After the addition, the reaction mixture was allowed to warm to −10° C. where it was stirred for 5 min. The resulting reaction mixture was again cooled back to −70° C. and then treated with methyl propiolate (7.57 g, 90 mmol). The reaction mixture was stirred for 15 h at −70° C. to −50° C. and then slowly treated with a solution of iodine (34.3 g, 135 mmol) in dry tetrahydrofuran (30 mL) while maintaining the temperature at −70° C. to −60° C. After addition of the iodine solution, the cooling bath was removed, and the reaction mixture was allowed to warm to 25° C. where it was stirred for 2 h. The reaction mixture was then poured into a solution consisting of a saturated aqueous ammonium chloride solution (400 mL) and ammonium hydroxide (100 mL), and the organic compound was extracted into ethyl acetate (3×200 mL). The combined organic extracts were successively washed with a saturated aqueous sodium thiosulfate solution (1×400 mL) and a saturated aqueous sodium chloride solution (1×400 mL). The organic layer was then dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 20/1 to 10/1 hexanes/diethyl ether) afforded (E)-3-cycloheptyl-2-iodo-acrylic acid methyl ester (17.86 g, 64%) as a colorless oil: EI-HRMS m/e calcd for C11H17IO2 (M+) 308.0273, found 308.0273. The resulting reaction mixture The resulting reaction mixture was stirred for 5-10 min the exothermic reaction the inside temperature below 50° C After complete addition the solution was stirred for 1 h In a separate reaction flask was stirred at 25° C. under argon for 10 min to obtain a clear solution After the addition to warm to −10° C. where it was stirred for 5 min The resulting reaction mixture was again cooled back to −70° C. The reaction mixture was stirred for 15 h at −70° C. to −50° C. while maintaining the temperature at −70° C. to −60° C the cooling bath was removed to warm to 25° C. where it was stirred for 2 h The reaction mixture was then poured into a solution the organic compound was extracted into ethyl acetate (3×200 mL) The combined organic extracts were successively washed with a saturated aqueous sodium thiosulfate solution (1×400 mL) The organic layer was then dried over anhydrous magnesium sulfate filtered concentrated in vacuo
Source ID: ord-5e542207d87e4cb1bf144aef50c22f4bConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-f9f038eb966a4a8aaa846e66f1920be2Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 1-Hydroxymethylcyclopentanamine was prepared according to Method B1c. The 2-hydroxyethylamine was sequentially reacted with SOCl2 and 2-methyl-4-nitrophenyl isothiocyanate according to Method C2a to give 2-(2-methyl-4-nitrophenylimino)-3-thia-1-azaspiro[4.4]nonane. The thiazolidine was reacted with cycloheptyl bromide according to Method D2e to give 2-(2-methyl-4-nitrophenylimino)-1-cycloheptyl-3-thia-1-azaspiro [4.4]nonane.
Source ID: ord-5948220c499f40c380bccbb8edcc1b60Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 1-Hydroxymethylcyclopentanamine was prepared according to Method B1c. The 2-hydroxyethylamine was sequentially reacted with SOCl2 and 2-methyl-4-nitrophenyl isothiocyanate according to Method C2a to give 2-(2-methyl-4-nitrophenylimino)-3-thia-1-azaspiro[4.4]nonane. The thiazolidine was reacted with cycloheptyl bromide according to Method D2e to give 2-(2-methyl-4-nitrophenylimino)-1-cycloheptyl-3-thia-1-azaspiro [4.4]nonane.
Source ID: ord-5948220c499f40c380bccbb8edcc1b60Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 2-Hydroxyethylamine was reacted with cycloheptyl bromide according to Method B2a to give N-cycloheptyl-N-(2-hydroxyethyl)amine. The alcohol was reacted with SOCl2 according to Method B7c to give N-cycloheptyl-N-(2-chloroethyl)ammonium chloride. The chloroethylamine was reacted with 2-methyl-4-nitrophenyl isothiocyanate to give 2-(2-methyl-4-nitrophenylimino)-3-cycloheptyl-1,3-thiazolidine.
Source ID: ord-f63e4eabee7f4de98724ce9d245b45f2Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 2-Hydroxyethylamine was reacted with cycloheptyl bromide according to Method B2a to give N-cycloheptyl-N-(2-hydroxyethyl)amine. The alcohol was reacted with SOCl2 according to Method B7c to give N-cycloheptyl-N-(2-chloroethyl)ammonium chloride. The chloroethylamine was reacted with 2-methyl-4-nitrophenyl isothiocyanate to give 2-(2-methyl-4-nitrophenylimino)-3-cycloheptyl-1,3-thiazolidine.
Source ID: ord-f63e4eabee7f4de98724ce9d245b45f2Conditions: temp:-70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of magnesium metal (4.81 g, 200 mmol) and dry tetrahydrofuran (10 mL) under argon was treated with a solution of 1,2-dibromoethane (0.94 g, 5 mmol) in dry tetrahydrofuran (5 mL). The resulting reaction mixture was stirred for 10 min to activate the magnesium metal. The reaction mixture was then treated dropwise with a solution of cycloheptyl bromide (17.7 g, 100 mmol) in dry tetrahydrofuran (30 mL), one-fifth portion over a period of 5 min. The resulting reaction mixture was stirred for 5-10 min to initiate the exothermic reaction. The remaining portion of the cycloheptyl bromide solution was then added dropwise while controlling the inside temperature below 50° C. After complete addition, the solution was stirred for 1 h and then diluted with dry tetrahydrofuran (80 mL). In a separate reaction flask, a mixture of lithium chloride (8.48 g, 200 mmol, predried at 130° C. under high vacuum for 3 h) and copper cyanide (8.96 g, 100 mmol) in dry tetrahydrofuran (110 mL) was stirred at 25° C. under argon for 10 min to obtain a clear solution. The reaction mixture was cooled to −70° C. and then slowly treated with the freshly prepared cycloheptylmagnesium bromide. After the addition, the reaction mixture was allowed to warm to −10° C. where it was stirred for 5 min. The resulting reaction mixture was again cooled back to −70° C. and then treated with methyl propiolate (7.57 g, 90 mmol). The reaction mixture was stirred for 15 h at −70° C. to −50° C. and then slowly treated with a solution of iodine (34.3 g, 135 mmol) in dry tetrahydrofuran (30 mL), with the temperature kept at −70° C. to −60° C. After addition of the iodine solution, the cooling bath was removed, and the reaction mixture was allowed to warm to 25° C. where it was stirred for 2 h. The reaction mixture was then poured into a solution consisting of a saturated aqueous ammonium chloride solution (400 mL) and ammonium hydroxide (100 mL), and the organic compound was extracted into ethyl acetate (3×200 mL). The combined organic extracts were successively washed with a saturated aqueous sodium thiosulfate solution (1×400 mL) and a saturated aqueous sodium chloride solution (1×400 mL). The organic layer was then dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 20/1 to 10/1 hexanes/diethyl ether) afforded (E)-3-cycloheptyl-2-iodo-acrylic acid methyl ester (17.86 g, 64%) as a colorless oil: EI-IIRMS m/e calcd for C11H17IO2 (M+) 308.0273, found 308.0273. The resulting reaction mixture The resulting reaction mixture was stirred for 5-10 min the exothermic reaction the inside temperature below 50° C After complete addition the solution was stirred for 1 h In a separate reaction flask was stirred at 25° C. under argon for 10 min to obtain a clear solution After the addition to warm to −10° C. where it was stirred for 5 min The resulting reaction mixture was again cooled back to −70° C. The reaction mixture was stirred for 15 h at −70° C. to −50° C. kept at −70° C. to −60° C the cooling bath was removed to warm to 25° C. where it was stirred for 2 h The reaction mixture was then poured into a solution the organic compound was extracted into ethyl acetate (3×200 mL) The combined organic extracts were successively washed with a saturated aqueous sodium thiosulfate solution (1×400 mL) The organic layer was then dried over anhydrous magnesium sulfate filtered concentrated in vacuo
Source ID: ord-c2d366eb401742cab9ce98b0eda8da0ePubChem References
These sources are listed in the compound's public database record.
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