213127-67-4

Basic information

• Product Name: (±)-((2-bromocyclohex-2-en-1-yl)oxy)benzene
• Synonyms: (±)-((2-bromocyclohex-2-en-1-yl)oxy)benzene
• CAS NO: 213127-67-4
• Molecular Weight: 253.139
• Mol File: 213127-67-4.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (±)-((2-bromocyclohex-2-en-1-yl)oxy)benzene(CAS DataBase Reference)
• NIST Chemistry Reference: (±)-((2-bromocyclohex-2-en-1-yl)oxy)benzene(213127-67-4)
• EPA Substance Registry System: (±)-((2-bromocyclohex-2-en-1-yl)oxy)benzene(213127-67-4)

Safety Data

• Hazardous Substances Data: 213127-67-4(Hazardous Substances Data)

Upstream product

• 109380-07-6 2-bromocyclohex-2-en-1-ol 
• 108-95-2 phenol 

Downstream Products

• 13130-19-3 1,2,3,4-tetrahydrodibenzo[b,d]furan 

Relevant articles and documents

Sequential O-Arylation/Lanthanide(III)-Catalyzed [3,3]-Sigmatropic Rearrangement of Bromo-Substituted Allylic Alcohols

Lanthanide(III)-catalyzed aryl-Claisen rearrangement of substrates bearing halo-substituted allyl groups, specifically 2-bromoallyl aryl ethers, afford ortho -2-bromoallylphenols. Aryl ether substrates were synthesized from brominated allylic alcohols via Mitsunobu reaction, Cu(II)-catalyzed arylation using potassium aryltrifluoroborate salts, or S N Ar reaction. Aryl-Claisen rearrangements proceeded in moderate to excellent yields using Eu(III) catalysis. The alkenylbromide functionality remains intact, illustrating the compatibility of synthetically important alkenylhalides during C-O/C-C σ-bond migration processes. Subsequent derivatization of the ortho -2-bromoallylphenol products through O-alkylation or C-arylation/alkenylation via Suzuki-Miyaura cross-coupling demonstrate the potential to access densely-functionalized molecules.