No renderable structure data available
CC1=CC2=C(O1)C(=CC=C2)BrChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 7-bromo-2-methyl-1-benzofuran |
|---|---|
| IUPAC Name | — |
| CAS Number | 57547-15-6 |
| Database ID | 12264721 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
7-bromo-2-methyl-1-benzofuran (CAS 57547-15-6) 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 12264721
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-a2de5796b65742208ff029a272e495bcConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-e6d3f88b111a4ecab955e2302960398eConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-a2de5796b65742208ff029a272e495bcConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-e6d3f88b111a4ecab955e2302960398eConditions: temp:-70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A stirred solution of 7-bromobenzofuran (493 mg, 2.5 mmol) in dry THF (5 mL) was cooled to −70° C. and 2M LDA in 1:1 THF/heptane (1.4 mL, 2.8 mmol) was added dropwise over 2 min. The mixture was stirred at −70° C. for 1 h and methyl iodide (0.19 mL, 3.0 mmol) was added. The mixture was stirred at −70° C. for 3 h and at 0° C. for 1 h. The mixture was poured into 5% aq HCl (60 mL) and extracted with ether (2×50 mL). The combined ether extracts were washed with sat'd aq NaHCO3 (20 mL) and dried over MgSO4. Removal of the solvent left an oil (470 mg) which was purified by chromatography on a 40-g silica cartridge eluted with hexanes to afford 7-bromo-2-methylbenzofuran (277 mg, 52%, estimated purity 80%). The mixture was stirred at −70° C. for 3 h and at 0° C. for 1 h extracted with ether (2×50 mL) The combined ether extracts were washed with sat'd aq NaHCO3 (20 mL) dried over MgSO4 Removal of the solvent left an oil (470 mg) which was purified by chromatography on a 40-g silica cartridge eluted with hexanes
Source ID: ord-9a39fbee365b4639aa6843a0305d7096Conditions: temp:-70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A stirred solution of 7-bromobenzofuran (493 mg, 2.5 mmol) in dry THF (5 mL) was cooled to −70° C. and 2M LDA in 1:1 THF/heptane (1.4 mL, 2.8 mmol) was added dropwise over 2 min. The mixture was stirred at −70° C. for 1 h and methyl iodide (0.19 mL, 3.0 mmol) was added. The mixture was stirred at −70° C. for 3 h and at 0° C. for 1 h. The mixture was poured into 5% aq HCl (60 mL) and extracted with ether (2×50 mL). The combined ether extracts were washed with sat'd aq NaHCO3 (20 mL) and dried over MgSO4. Removal of the solvent left an oil (470 mg) which was purified by chromatography on a 40-g silica cartridge eluted with hexanes to afford 7-bromo-2-methylbenzofuran (277 mg, 52%, estimated purity 80%). The mixture was stirred at −70° C. for 3 h and at 0° C. for 1 h extracted with ether (2×50 mL) The combined ether extracts were washed with sat'd aq NaHCO3 (20 mL) dried over MgSO4 Removal of the solvent left an oil (470 mg) which was purified by chromatography on a 40-g silica cartridge eluted with hexanes
Source ID: ord-9a39fbee365b4639aa6843a0305d7096Conditions: temp:-70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A stirred solution of 7-bromobenzofuran (493 mg, 2.5 mmol) in dry THF (5 mL) was cooled to −70° C. and 2M LDA in 1:1 THF/heptane (1.4 mL, 2.8 mmol) was added dropwise over 2 min. The mixture was stirred at −70° C. for 1 h and methyl iodide (0.19 mL, 3.0 mmol) was added. The mixture was stirred at −70° C. for 3 h and at 0° C. for 1 h. The mixture was poured into 5% aq HCl (60 mL) and extracted with ether (2×50 mL). The combined ether extracts were washed with sat'd aq NaHCO3 (20 mL) and dried over MgSO4. Removal of the solvent left an oil (470 mg) which was purified by chromatography on a 40-g silica cartridge eluted with hexanes to afford 7-bromo-2-methylbenzofuran (277 mg, 52%, estimated purity ˜80%). The mixture was stirred at −70° C. for 3 h and at 0° C. for 1 h extracted with ether (2×50 mL) The combined ether extracts were washed with sat'd aq NaHCO3 (20 mL) dried over MgSO4 Removal of the solvent left an oil (470 mg) which was purified by chromatography on a 40-g silica cartridge eluted with hexanes
Source ID: ord-eb4563c8c3f7406b9b2f432bb22c7c7cConditions: temp:-70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A stirred solution of 7-bromobenzofuran (493 mg, 2.5 mmol) in dry THF (5 mL) was cooled to −70° C. and 2M LDA in 1:1 THF/heptane (1.4 mL, 2.8 mmol) was added dropwise over 2 min. The mixture was stirred at −70° C. for 1 h and methyl iodide (0.19 mL, 3.0 mmol) was added. The mixture was stirred at −70° C. for 3 h and at 0° C. for 1 h. The mixture was poured into 5% aq HCl (60 mL) and extracted with ether (2×50 mL). The combined ether extracts were washed with sat'd aq NaHCO3 (20 mL) and dried over MgSO4. Removal of the solvent left an oil (470 mg) which was purified by chromatography on a 40-g silica cartridge eluted with hexanes to afford 7-bromo-2-methylbenzofuran (277 mg, 52%, estimated purity ˜80%). The mixture was stirred at −70° C. for 3 h and at 0° C. for 1 h extracted with ether (2×50 mL) The combined ether extracts were washed with sat'd aq NaHCO3 (20 mL) dried over MgSO4 Removal of the solvent left an oil (470 mg) which was purified by chromatography on a 40-g silica cartridge eluted with hexanes
Source ID: ord-eb4563c8c3f7406b9b2f432bb22c7c7cConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Beginning with 1.0 gm (4.74 mMol) 2-methyl-7-bromobenzofuran and 1.01 gm (4.98 mMol) 1-benzyl-3-methyl-4-oxopiperidine, 1.06 gm of the desired compound was prepared as an orange oil essentially as described in EXAMPLE 19.
Source ID: ord-797153a5596d4279a8d0ef0eab866615Conditions: temp:-70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A stirred solution of 7-bromobenzofuran (493 mg, 2.5 mmol) in dry THF (5 mL) was cooled to −70° C. and 2M LDA in 1:1 THF/heptane (1.4 mL, 2.8 mmol) was added dropwise over 2 min. The mixture was stirred at −70° C. for 1 h and methyl iodide (0.19 mL, 3.0 mmol) was added. The mixture was stirred at −70° C. for 3 h and at 0° C. for 1 h. The mixture was poured into 5% aq HCl (60 mL) and extracted with ether (2×50 mL). The combined ether extracts were washed with sat'd aq NaHCO3 (20 mL) and dried over MgSO4. Removal of the solvent left an oil (470 mg) which was purified by chromatography on a 40-g silica cartridge eluted with hexanes to afford 7-bromo-2-methylbenzofuran (277 mg, 52%, estimated purity ˜80%). The mixture was stirred at −70° C. for 3 h and at 0° C. for 1 h extracted with ether (2×50 mL) The combined ether extracts were washed with sat'd aq NaHCO3 (20 mL) dried over MgSO4 Removal of the solvent left an oil (470 mg) which was purified by chromatography on a 40-g silica cartridge eluted with hexanes
Source ID: ord-7bbd754d0c784504ada9364a27969f11PubChem References
These sources are listed in the compound's public database record.
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