436848-01-0

Basic information

• Product Name: 4-bromo-1-(tert-butoxycarbonyloxy)benzene
• Synonyms: 4-bromo-1-(tert-butoxycarbonyloxy)benzene
• CAS NO: 436848-01-0
• Molecular Weight: 273.126
• Mol File: 436848-01-0.mol

Chemical Properties

• CAS DataBase Reference: 4-bromo-1-(tert-butoxycarbonyloxy)benzene(CAS DataBase Reference)
• NIST Chemistry Reference: 4-bromo-1-(tert-butoxycarbonyloxy)benzene(436848-01-0)
• EPA Substance Registry System: 4-bromo-1-(tert-butoxycarbonyloxy)benzene(436848-01-0)

Safety Data

• Hazardous Substances Data: 436848-01-0(Hazardous Substances Data)

Upstream product

• 106-41-2 4-bromo-phenol 
• 24424-99-5 di-tert-butyl dicarbonate 
• 1187442-17-6 tert-butyl 2,4-dibromophenyl carbonate 

Downstream Products

• 71597-85-8 (p-hydroxyphenyl)boronic acid 
• 1333434-82-4 tert-butyl (4-(2-methylquinolin-8-yl)phenyl)carbonate 
• 106-41-2 4-bromo-phenol 

Relevant articles and documents

Facile tert-butoxycarbonylation of alcohols, phenols, and amines using BiCl3 as a mild and efficient catalyst

Facile tert-butoxycarbonylation of alcohols, phenols, and amines is described by treatment of alcohols, phenols, and amines with di-tert-butyl dicarbonate in the presence of a catalytic amount of bismuth(III) chloride, a mild and efficient catalyst, at room temperature in excellent yields. Copyright Taylor & Francis Group, LLC.

Preparation method of hydroxyphenylboronic acid

The invention discloses a preparation method of hydroxyphenylboronic acid, which belongs to the technical field of boric acid synthesis in medical intermediates. The method comprises the following steps: starting from bromophenol, carrying out BOC, trimethylsilyl or benzyl protection, forming a Grignard reagent, reacting with borate, or carrying out one-pot reaction with borate and n-butyllithium,and hydrolyzing to obtain hydroxyphenylboronic acid. According to the invention, cheap and easily available protecting groups are adopted, so that the protecting groups are easy to remove during boronation reaction hydrolysis, industrial amplification is easy to realize, batch production is carried out on the scale of dozens of kilograms, and the process stability is good.

NOVEL SELECTIVE 11-BETA-HYDROXYSTEROID DEHYDROGENASE TYPE 1

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MgBr 2 · OEt 2: A Lewis Acid Catalyst for the O - And N -Boc Protection of Phenols and Amines

MgBr2 · OEt2 efficiently catalyzes the O- and N-tert-butoxycarbonylation of functionalized phenols and amines. The presented procedure is operationally simple and done under solvent-free conditions. GRAPHICAL ABSTRACT.

Cobalt-Catalyzed Cross-Coupling of 3- and 4-Iodopiperidines with Grignard Reagents

A cobalt-catalyzed cross-coupling between 3- and 4-iodopiperidines and Grignard reagents is disclosed. The reaction is an efficient, cheap, chemoselective, and flexible way to functionalize piperidines. This coupling was used as the key step to realize a short synthesis of (±)-preclamol. Some mechanistic investigations were conducted that highlight the formation of radical intermediates. Scaffold synthesis: A cobalt-catalyzed cross-coupling between iodopiperidines and Grignard reagents is reported (see scheme; PG=protecting group). A large variety of 3- and 4-substituted piperidines were synthesized and the method was applied to a short synthesis of (±)-preclamol. This work constitutes one of the rare examples of cross-couplings involving 3-halogeno piperidines.

Iron- and cobalt-catalyzed arylation of azetidines, pyrrolidines, and piperidines with grignard reagents

Iron- and cobalt-catalyzed cross-couplings between iodo-azetidines, -pyrrolidines, -piperidines, and Grignard reagents are disclosed. The reaction is efficient, cheap, chemoselective and tolerates a large variety of (hetero)aryl Grignard reagents.

A new, efficient, and catalyst-free microwave-assisted approach for formation of O-tert-butoxy carbonates

A new simple, efficient, greener, and catalyst-free chemoselective protocol for the O-tert-butoxycarbonylation of various structurally diverse hydroxy compounds was carried out with (Boc)2O under microwave radiation. The corresponding O-tertbutoxy carbonates were obtained in good to excellent yields in a short reaction time without any side reactions.

Mixed metal MgO-ZrO2 nanoparticle-catalyzed O-tert-Boc protection of alcohols and phenols under solvent-free conditions

An environmentally benign method for O-tert-Boc protection of alcohols and phenols catalyzed by MgO-ZrO2 nanoparticles under solvent-free conditions is described. A variety of phenols, alcohols (aliphatic and aromatic) were converted to corresponding O-tert-Boc products in good to excellent yield (50-95%). The present protocol is expedient, simple, and efficient under solvent-free conditions. The MgO-ZrO2 Nps are easily prepared from inexpensive precursors, and are reusable, recyclable and chemoselective. Copyright 2012 John Wiley & Sons, Ltd. Copyright

An eco-sustainable erbium(iii)-catalyzed method for formation/cleavage of O-tert-butoxy carbonates

A new simple and effective method for the formation/cleavage of O-tert-butoxy carbonates of alcohols and phenols is proposed. Mesoporous silica-supported Er(iii) (ErIII-MCM-41) was used as an efficient and reusable solid catalyst in the solvent-free ultrasound-assisted synthesis of Boc-carbonate derivatives of a wide range of alcohols and phenols. The fast, selective deprotection of Boc-derivatives is achieved with a very low amount of Er(OTf)3 in ethanol under microwave irradiation. Therefore, the entire protection/de-protection process is very attractive, from the point of view of sustainability.

Preparation of polyfunctional arylmagnesium, arylzinc, and benzylic zinc reagents by using magnesium in the presence of LiCl

The presence of LiCl considerably facilitates the insertion of magnesium into various aromatic and heterocyclic bromides. Several functional groups, such as -OBoc, -OTs, -Cl, -F, -CF3, -OMe, -NMe2, and -N 2NR2, are well tolerated. The presence of a cyano group leads in some cases to competitive reduction of the organic halide to the corresponding ArH compound. The presence of sensitive groups such as methyl or ethyl ester is tolerated upon in situ trapping of the intermediate magnesium reagent with ZnCl2. This method can also be applied to the preparation of functionalized benzylic zinc reagents from benzylic chlorides. In the case of di- or tribromoaryl derivatives, directing groups such as -OPiv, -OTs, -N2NR2, or -OAc orient the zinc insertion (Zn/LiCl) to the ortho-position, while the reaction with Mg/LiCl or Mg/LiCl/ZnCl 2 leads to regioselective insertion into the para-carbon-bromine bond. Large-scale experiments (20-100 mmol) for all of the metalation procedures are described.