Reaction #4125703
Related Literature (1)
openreactiondata ↗doi:10.1039/C8SC04228D
Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-3e8744424d3b4bc28ce81e9f468433caNo renderable structure data available
BrC1C([H])=C([H])C(=C([H])C=1OC([H])([H])C([H])([H])Br)BrChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 1,4-bis(bromanyl)-2-(2-bromoethyloxy)benzene |
|---|---|
| IUPAC Name | — |
| CAS Number | 377091-18-4 |
| Database ID | 11473835 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
1,4-bis(bromanyl)-2-(2-bromoethyloxy)benzene (CAS 377091-18-4) 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 11473835
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-3e8744424d3b4bc28ce81e9f468433caConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-37b6f6eb765c46ef9d61f160e1425250Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 1,4-dibromo-2-(2-bromoethoxy)benzene (136) (922 mg, 2.57 mmol) was dissolved in 25 ml dry THF. After cooled down to −78° C., a solution of 2.5M n-BuLi (1.23 ml, 1.2 q) in hexane was added dropwise. The reaction mixture was stirred at −78° C. for 4 h before poured into ice-water. After extracted twice with ethyl acetate, the org. phase was washed with brine, dried over sodium sulfate and then concentrated to give 504 mg (purity ca 80%) 6-bromo-2,3-dihydrobenzo[b]furan (137) as dark brow oil which was used directly for further reaction. After extracted twice with ethyl acetate phase was washed with brine dried over sodium sulfate concentrated
Source ID: ord-f76f6ebd679740baa486b91732a5048eConditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 1,4-dibromo-2-(2-bromoethoxy)benzene (136) (922 mg, 2.57 mmol) was dissolved in 25 ml dry THF. After cooled down to −78° C., a solution of 2.5M n-BuLi (1.23 ml, 1.2 q) in hexane was added dropwise. The reaction mixture was stirred at −78° C. for 4 h before poured into ice-water. After extracted twice with ethyl acetate, the org. phase was washed with brine, dried over sodium sulfate and then concentrated to give 504 mg (purity ca 80%) 6-bromo-2,3-dihydrobenzo[b]furan (137) as dark brow oil which was used directly for further reaction. After extracted twice with ethyl acetate phase was washed with brine dried over sodium sulfate concentrated
Source ID: ord-f76f6ebd679740baa486b91732a5048eConditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of 2,5-dibromophenol (134) (1.26 g, 5 mmol) and 1,2-dibromoethane (135) (431 μl, 5 mmol) in 5 ml 1N NaOH was stirred at 80° C. for 40 h. After cooling down, the reaction mixture was extracted with diethyl ether. Org. phase was washed with 1 N NaOH and brine subsequently. Org. phase was dried over sodium sulfate concentrated to give 922 mg (yield 51%, purity ca 90%) 1,4-dibromo-2-(2-bromoethoxy)benzene (136) as orange-red oil which was used directly for further reaction without purification. After cooling down the reaction mixture was extracted with diethyl ether phase was washed with 1 N NaOH and brine subsequently phase was dried over sodium sulfate concentrated
Source ID: ord-8f2c50bb3f874bdb85ad6f5f69a3578fConditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 1,4-dibromo-2-(2-bromoethoxy)benzene (136) (922 mg, 2.57 mmol) was dissolved in 25 ml dry THF. After cooled down to −78° C., a solution of 2.5M n-BuLi (1.23 ml, 1.2 q) in hexane was added dropwise. The reaction mixture was stirred at −78° C. for 4 h before poured into ice-water. After extracted twice with ethyl acetate, the org. phase was washed with brine, dried over sodium sulfate and then concentrated to give 504 mg (purity ca 80%) 6-bromo-2,3-dihydrobenzo[b]furan (137) as dark brow oil which was used directly for further reaction. After extracted twice with ethyl acetate phase was washed with brine dried over sodium sulfate concentrated
Source ID: ord-a9f701c857774c53b174c37a0dc1627dConditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 1,4-dibromo-2-(2-bromoethoxy)benzene (136) (922 mg, 2.57 mmol) was dissolved in 25 ml dry THF. After cooled down to −78° C., a solution of 2.5M n-BuLi (1.23 ml, 1.2 q) in hexane was added dropwise. The reaction mixture was stirred at −78° C. for 4 h before poured into ice-water. After extracted twice with ethyl acetate, the org. phase was washed with brine, dried over sodium sulfate and then concentrated to give 504 mg (purity ca 80%) 6-bromo-2,3-dihydrobenzo[b]furan (137) as dark brow oil which was used directly for further reaction. After extracted twice with ethyl acetate phase was washed with brine dried over sodium sulfate concentrated
Source ID: ord-a9f701c857774c53b174c37a0dc1627dConditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of 2,5-dibromophenol (134) (1.26 g, 5 mmol) and 1,2-dibromoethane (135) (431 μl, 5 mmol) in 5 ml 1N NaOH was stirred at 80° C. for 40 h. After cooling down, the reaction mixture was extracted with diethyl ether. Org. phase was washed with 1 N NaOH and brine subsequently. Org. phase was dried over sodium sulfate concentrated to give 922 mg (yield 51%, purity ca 90%) 1,4-dibromo-2-(2-bromoethoxy)benzene (136) as orange-red oil which was used directly for further reaction without purification. After cooling down the reaction mixture was extracted with diethyl ether phase was washed with 1 N NaOH and brine subsequently phase was dried over sodium sulfate concentrated
Source ID: ord-3d97d962c25e40d3ab3e26eae504835eConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-3e8744424d3b4bc28ce81e9f468433caConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-37b6f6eb765c46ef9d61f160e1425250Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 1,4-dibromo-2-(2-bromoethoxy)benzene (136) (922 mg, 2.57 mmol) was dissolved in 25 ml dry THF. After cooled down to −78° C., a solution of 2.5M n-BuLi (1.23 ml, 1.2q) in hexane was added dropwise. The reaction mixture was stirred at −78° C. for 4 h before poured into ice-water. After extracted twice with ethyl acetate, the org. phase was washed with brine, dried over sodium sulfate and then concentrated to give 504 mg (purity ca 80%) 6-bromo-2,3-dihydrobenzo[b]furan (137) as dark brow oil which was used directly for further reaction. After extracted twice with ethyl acetate phase was washed with brine dried over sodium sulfate concentrated
Source ID: ord-0580feeed563403b8be776a14b40532aConditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of 2,5-dibromophenol (134) (1.26 g, 5 mmol) and 1,2-dibromoethane (135) (431 μl, 5 mmol) in 5 ml 1N NaOH was stirred at 80° C. for 40 h. After cooling down, the reaction mixture was extracted with diethyl ether. Org. phase was washed with 1 N NaOH and brine subsequently. Org. phase was dried over sodium sulfate concentrated to give 922 mg (yield 51%, purity ca 90%) 1,4-dibromo-2-(2-bromoethoxy)benzene (136) as orange-red oil which was used directly for further reaction without purification. After cooling down the reaction mixture was extracted with diethyl ether phase was washed with 1 N NaOH and brine subsequently phase was dried over sodium sulfate concentrated
Source ID: ord-ff981cb3fd21463586053632b956652dPubChem References
These sources are listed in the compound's public database record.
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