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
• Article Data: 4

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

4,5-Dibromo-2-benzoylpyrrole is used in preparation of 2,3-Dibromo-5-benzoyl Pyrrole via amidation of morpholine with Benzoyl Chloride, followed by Friedel-Crafts reaction with pyrrole and substitution with Br2.

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.

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.