100791-83-1

Basic information

• Product Name: Dimethyl (4R,5R)-2-[(S)-1-bromoethyl]-2-(4-methoxyphenyl)-1,3-dioxolane-4,5-dicarboxylate
• Synonyms: Dimethyl (4R,5R)-2-[(S)-1-bromoethyl]-2-(4-methoxyphenyl)-1,3-dioxolane-4,5-dicarboxylate
• CAS NO: 100791-83-1
• Molecular Weight: 403.227
• Mol File: 100791-83-1.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Dimethyl (4R,5R)-2-[(S)-1-bromoethyl]-2-(4-methoxyphenyl)-1,3-dioxolane-4,5-dicarboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: Dimethyl (4R,5R)-2-[(S)-1-bromoethyl]-2-(4-methoxyphenyl)-1,3-dioxolane-4,5-dicarboxylate(100791-83-1)
• EPA Substance Registry System: Dimethyl (4R,5R)-2-[(S)-1-bromoethyl]-2-(4-methoxyphenyl)-1,3-dioxolane-4,5-dicarboxylate(100791-83-1)

Safety Data

• Hazardous Substances Data: 100791-83-1(Hazardous Substances Data)

Upstream product

• 121-97-1 4-Methoxypropiophenone 
• 13171-64-7 Dimethyl D-tartrate 
• 100791-76-2 (4S,5S)-2-Ethyl-2-(4-methoxy-phenyl)-[1,3]dioxolane-4,5-dicarboxylic acid dimethyl ester 
• 608-68-4 dimethyl L-tartrate 
• 100791-76-2 (4R,5R)-2-ethyl-2-(4-methoxyphenyl)-1,3-dioxolane-4,5-dicarboxylic acid dimethyl ester 

Downstream Products

• 119492-57-8 (S)-2-Bromo-1-(4-methoxyphenyl)propan-1-one 
• 21086-33-9 (R)-2-Bromo-1-(4-methoxyphenyl)propan-1-one 

Relevant articles and documents

Enantioselective synthesis of α-bromo acid derivatives and bromohydrins from tartrate derived bromoacetals

Bromination of the acetals 4 derived from aryl alkyl ketones, ArCOR, and (2R,3R)-tartaric acid results in bromoacetals 5 with 78-90% de. Hydrolysis of those compounds with Ar = 4-methoxyphenyl or 3-bromo-4-methoxyphenyl results, after recrystallisation, in α-bromoketones 8 with 66-98% ee which are shown to undergo the Baeyer-Villiger oxidation to α-bromoesters 9 with minimal racemisation, α-Bromoketone 8d is shown to undergo carbonyl reduction to threo-bromohydrin 15 with retention of stereochemistry.

Asymmetrische Bromierung enantiomerenreiner Acetale von Alkylarylketonen

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