50372-61-7

Basic information

• Product Name: 2,3-Dibromo-5-benzoylpyrrole
• Synonyms: (4,5-Dibromo-1H-pyrrol-2-yl)phenylmethanone;4,5-Dibromo-2-benzoylpyrrole;Methanone,(4,5-dibroMo-1H-pyrrol-2-yl)phenyl-
• CAS NO: 50372-61-7
• Molecular Formula: C₁₁H₇Br₂NO
• Molecular Weight: 329
• Mol File: 50372-61-7.mol

Chemical Properties

• Boiling Point: 430.963 °C at 760 mmHg
• Flash Point: 214.439 °C
• Appearance: /
• Density: 1.845
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2,3-Dibromo-5-benzoylpyrrole(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-Dibromo-5-benzoylpyrrole(50372-61-7)
• EPA Substance Registry System: 2,3-Dibromo-5-benzoylpyrrole(50372-61-7)

Safety Data

• Hazardous Substances Data: 50372-61-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2,3-Dibromo-5-benzoylpyrrole is used as an intermediate compound for the synthesis of various pharmaceuticals. Its unique structure allows it to be a key component in the development of new drugs with potential therapeutic applications.
Used in Chemical Synthesis:
In the field of organic chemistry, 2,3-Dibromo-5-benzoylpyrrole is used as a building block for the creation of more complex molecules. Its reactive sites, such as the bromine atoms and the benzoyl group, can be further modified to produce a wide range of chemical products.
Used in Research and Development:
2,3-Dibromo-5-benzoylpyrrole is also utilized in research and development settings, where it can be employed to study various chemical reactions and mechanisms. Its unique properties make it an interesting subject for scientific investigation, potentially leading to new discoveries and advancements in the field of chemistry.
In the provided materials, 2,3-Dibromo-5-benzoylpyrrole is specifically used in the preparation of another compound, 4,5-Dibromo-2-benzoylpyrrole, through a series of chemical reactions involving amidation, Friedel-Crafts reaction, and substitution with Br2. This demonstrates its utility as a starting material in the synthesis of complex organic compounds.

Synthetic route

phenyl(1H-pyrrol-2-yl)methanone (7697-46-3) → 2,3-dibromo-5-benzoylpyrrole (50372-61-7)

Conditions	Yield
With copper(ll) bromide In acetonitrile for 48h; Ambient temperature;	85%
With bromine In dichloromethane 0 deg C to RT, 2.5 h;	77%
With bromine In dichloromethane	76.5%

cycl-isopropylidene cyclopropane-1,1-dicarboxylate (5617-70-9) + 2,3-dibromo-5-benzoylpyrrole (50372-61-7) → C19H16Br2NO5(1-)*Na(1+) (80965-17-9)

Conditions	Yield
With sodium hydride 1.) DMF, RT, 1 h, 2.) 75-80 deg C, 4 h; Multistep reaction;

2,3-dibromo-5-benzoylpyrrole (50372-61-7) → Ketorolac (74103-06-3)

Conditions	Yield
Multi-step reaction with 4 steps 1: 1.) NaH / 1.) DMF, RT, 1 h, 2.) 75-80 deg C, 4 h 2: HCl / 5 h / 0 deg C to RT 4: magnesium oxide, H2 / 5percent Pd/C / H2O; methanol / 2 h / 760 Torr / Ambient temperature View Scheme

2,3-dibromo-5-benzoylpyrrole (50372-61-7) → 5-benzoyl-7-bromo-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acid (84023-60-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: 1.) NaH / 1.) DMF, RT, 1 h, 2.) 75-80 deg C, 4 h 2: HCl / 5 h / 0 deg C to RT View Scheme

2,3-dibromo-5-benzoylpyrrole (50372-61-7) → methyl 5-benzoyl-7-bromo-1,2-dihydro-3H-pyrrolo<1,2-a>pyrrole-1-carboxylate (80965-19-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: 1.) NaH / 1.) DMF, RT, 1 h, 2.) 75-80 deg C, 4 h 2: HCl / 5 h / 0 deg C to RT 3: 1.) NaH / 1.) DMF, 20 min, 2.) 75 deg C, 1.5 h View Scheme

2,3-dibromo-5-benzoylpyrrole (50372-61-7) → dimethyl 5-benzoyl-7-bromo-1,2-dihydro-3H-pyrrolo<1,2-a>pyrrole-1,1-dicarboxylate (80965-20-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: 1.) NaH / 1.) DMF, RT, 1 h, 2.) 75-80 deg C, 4 h 2: HCl / 5 h / 0 deg C to RT 3: 1.) NaH / 1.) DMF, 20 min, 2.) 75 deg C, 1.5 h View Scheme

2,3-dibromo-5-benzoylpyrrole (50372-61-7) → dimethyl[2-(2,3-dibromo-5-benzoylpyrrol-1-yl)ethyl]malonate (80965-18-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) NaH / 1.) DMF, RT, 1 h, 2.) 75-80 deg C, 4 h 2: HCl / 5 h / 0 deg C to RT View Scheme

spiro[2.5]-5,7-dioxa-6,6-dimethyloctane-4,8-dione + flurosil + 2,3-dibromo-5-benzoylpyrrole (50372-61-7) → dimethyl[2-(2,3-dibromo-5-benzoylpyrrol-1-yl)ethyl]malonate (80965-18-0)

Conditions	Yield
With hydrogenchloride In N-methyl-acetamide; methanol; diethyl ether; mineral oil

Upstream product

• 7697-46-3 phenyl(1H-pyrrol-2-yl)methanone 

Downstream Products

• 80965-18-0 dimethyl[2-(2,3-dibromo-5-benzoylpyrrol-1-yl)ethyl]malonate 
• 80965-20-4 dimethyl 5-benzoyl-7-bromo-1,2-dihydro-3H-pyrrolo<1,2-a>pyrrole-1,1-dicarboxylate 
• 80965-19-1 methyl 5-benzoyl-7-bromo-1,2-dihydro-3H-pyrrolo<1,2-a>pyrrole-1-carboxylate 
• 84023-60-9 5-benzoyl-7-bromo-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acid 
• 74103-06-3 Ketorolac 
• 80965-17-9 C₁₉H₁₆Br₂NO₅^(1-)*Na⁽¹⁺⁾ 

Relevant articles and documents

Oxidative Halogenation of Substituted Pyrroles with Cu(II). Part III. Bromination and Chlorination of 2-Benzoylpyrrole

The bromination of 2-benzoylpyrrole with copper (II) bromide in the homogenous and heterogenous phase is described, giving 4- and 5-monobromo derivatives whose ratio decreases as the temperature is increased.The same reaction with copper(II) chloride in acetonitrile at 60 deg C produces 5-chloro-2-benzoylpyrrole as the major product. 4,5-Dihalopyrroles in good yields are obtained with an excess of halogenating agent.

Novel Syntheses of 5-Aroyl-1,2-dihydro-3H-pyrrolopyrrole-1-carboxylic Acids

A fundamentally new approach to the synthesis of the title compounds was devised in which the crucial step was the intramolecular displacement of methanesulfinate ion or bromide ion by the sodium enolates of properly disposed substituted malonate esters such as 13a-13c and 20.As integral parts of the above process, a new four-carbon alkylation of the pyrrole nitrogen atom, a novel synthesis of 2-(methylthio)pyrroles, and the use of the dimethylsulfonium moiety as meta directing group in the pyrrole system were developed.

Processes for preparing 5-benzoyl-7-halo-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acids

5-benzoyl-7-halo-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acids, represented by the formula STR1 and the pharmaceutically acceptable non-toxic esters and salts thereof, wherein: R is hydrogen or lower alkyl; X is hydrogen, lower alkyl, lower alkoxyl, lower alkoxycarbonyl, carboxyl, lower alkylcarbonyl, sulfonic acid, sulfonic acid alkyl ester, fluoro, chloro, or bromo; and Y is chloro or bromo, which are novel, and 5-benzoyl-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acids which are represented by the formula STR2 wherein X and R are as above defined except that X cannot be chloro or bromo, are prepared by decarboxylation of the corresponding 1,1 dicarboxylates. Intermediates in said preparation are also disclosed.