1044572-77-1

Basic information

• Product Name: tert-butyl 4-[(4-methoxyphenyl)sulfinyl]benzoate
• Synonyms: tert-butyl 4-[(4-methoxyphenyl)sulfinyl]benzoate
• CAS NO: 1044572-77-1
• Molecular Weight: 332.42
• Mol File: 1044572-77-1.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: tert-butyl 4-[(4-methoxyphenyl)sulfinyl]benzoate(CAS DataBase Reference)
• NIST Chemistry Reference: tert-butyl 4-[(4-methoxyphenyl)sulfinyl]benzoate(1044572-77-1)
• EPA Substance Registry System: tert-butyl 4-[(4-methoxyphenyl)sulfinyl]benzoate(1044572-77-1)

Safety Data

• Hazardous Substances Data: 1044572-77-1(Hazardous Substances Data)

Upstream product

• 31401-23-7 p-methoxybenzenesulfinyl chloride 
• 850306-26-2 4-(tert-butoxycarbonyl)phenylmagnesium chloride 

Downstream Products

• 1044572-88-4 4-(4-methoxy-benzenesulfinyl)-3-trimethylsilanylethynylbenzoic acid tert-butyl ester 
• 1044572-86-2 ((2-((4-methoxyphenyl)sulfinyl)-5-(trifluoromethyl)phenyl)ethynyl)trimethylsilane 
• 1309446-25-0 tert-butyl 4-((4-methoxyphenyl)sulfinyl)-3-(phenylethynyl)benzoate 

Relevant articles and documents

Difunctionalisation of arenes and heteroarenes by directed metallation and sulfoxide-magnesium exchange

The aryl sulfoxide moiety allows an expedient two-step difunctionalisation of readily available diaryl sulfoxides. Highly functionalised 1,2,4-trisubstituted arenes and difunctionalised heteroarenes (furans, thiophenes, benzofurans and pyridines) were prepared in a two-step sequence, triggered by an aryl sulfoxide group. In the first step, the sulfoxide moiety acts as a metallation-directing group, allowing smooth ortho-magnesiation with TMPMgCl.LiCl (TMP=tetramethylpiperidine). After a quenching reaction with an electrophile, the resulting sulfoxide is converted into a second magnesium reagent with iPrMgCl.LiCl (sulfoxide-magnesium exchange), which can be trapped with various electrophiles. Highly chemoselective TMPMgCl.LiCl and iPrMgCl.LiCl are compatible with a broad range of functional groups (e.g., F, Cl, CF 3, CN, CO2tBu, alkynyl, ethers, thioethers). Large-scale reactions (25-40 mmol) and the preparation of fully functionalised furans and thiophenes are also reported. Successful exchange: Highly functionalised 1,2,4-trisubstituted arenes and difunctionalised heteroarenes were prepared in a two-step sequence, triggered by an aryl sulfoxide group. The chemoselective reagents used, TMPMgCl.LiCl (TMP=tetramethylpiperidine) and iPrMgCl.LiCl, are compatible with a broad range of functional groups (see scheme; E=electrophile.)

Meta- and para-difunctionalization of arenes via a sulfoxide-magnesium exchange reaction

(Chemical Equation Presented) The aryl sulfoxide moiety (ArSO) allows an expedient two-step meta-, para-difunctionalization of readily available diaryl sulfoxides. In the first step, the sulfoxide plays the role of a directing metalation group. In the second step, triggered by i-PrMgCl·LiCl, it becomes a leaving group and undergoes a regioselective sulfoxide-magnesium exchange.