630120-19-3

Basic information

• Product Name: 2-bromo-6-methoxy-4-methylphenylacetaldehyde
• Synonyms: 2-bromo-6-methoxy-4-methylphenylacetaldehyde
• CAS NO: 630120-19-3
• Molecular Weight: 243.1
• Mol File: 630120-19-3.mol

Chemical Properties

• CAS DataBase Reference: 2-bromo-6-methoxy-4-methylphenylacetaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 2-bromo-6-methoxy-4-methylphenylacetaldehyde(630120-19-3)
• EPA Substance Registry System: 2-bromo-6-methoxy-4-methylphenylacetaldehyde(630120-19-3)

Safety Data

• Hazardous Substances Data: 630120-19-3(Hazardous Substances Data)

Upstream product

• 1064653-82-2 1-Bromo-3-methoxy-2-((E)-2-methoxy-vinyl)-5-methyl-benzene 
• 4009-98-7 (methoxymethyl)triphenylphosphonium chloride 
• 133129-29-0 2-bromo-6-methoxy-4-methylbenzaldehyde 

Downstream Products

• 630120-22-8 2-(2-bromo-6-methoxy-4-methylphenyl)ethanol 
• 630120-24-0 methanesulfonic acid 2-(2-bromo-6-methoxy-4-methyl-phenyl)-ethyl ester 
• 630120-33-1 (3S,6R,7aR)-6-[2-(2-bromo-6-methoxy-4-methylphenyl)ethyl]-7a-isobutyl-3-isopropyl-6-methyltetrahydropyrrolo[2,1-b]oxazol-5-one 
• 630120-32-0 (3S,7aR)-6-[2-(2-bromo-6-methoxy-4-methylphenyl)ethyl]-7a-isobutyl-3-isopropyltetrahydropyrrolo[2,1-b]oxazol-5-one 
• 630120-27-3 1-bromo-2-(2-iodoethyl)-3-methoxy-5-methylbenzene 

Relevant articles and documents

Synthesis of (+/-)-hamigeran B, (-)-hamigeran B, and (+/-)-1-epi-hamigeran B: use of bulky silyl groups to protect a benzylic carbon-oxygen bond from hydrogenolysis.

Enone 42 was converted into diene 56, which was then subjected to hydrogenation. Use of the tert-butyldimethylsiloxy groups enforces facial selectivity and protects the C(5) oxygen from hydrogenolysis. The resulting product (55) is easily converted into hamigeran B (1), a marine natural product with powerful activity against herpes and polio viruses. Optically pure enone 73 was made by use of a Meyers' auxiliary and converted into (-)-hamigeran B with the natural absolute configuration.

Synthesis of natural (-)-hamigeran B

Alkylation of lactam 10, first with iodide 15 and then with MeI, gave mainly (18:1) lactam 18. This was converted by treatment with t-BuLi and then with aqueous base into enone 4, which was elaborated into (-)-hamigeran B. A key feature of the last part of the synthesis is the use of t-BuMe 2Si-groups (as in intermediate 24) both to direct hydrogenation from the appropriate face and to protect the benzylic C-O bond from hydrogenolysis.