1-(Benzenesulfonyl)-4-bromo-1H-pyrrole-2-carbaldehyde

Base Information

• Chemical Name: 1-(Benzenesulfonyl)-4-bromo-1H-pyrrole-2-carbaldehyde
• CAS No.: 138371-99-0
• Molecular Formula: C11H8BrNO3S
• Molecular Weight: 314.159
• DSSTox Substance ID: DTXSID60568030
• Nikkaji Number: J793.269C
• Wikidata: Q82454153
• Mol file: 138371-99-0.mol

Synonyms:138371-99-0;4-Bromo-1-(phenylsulfonyl)-1H-pyrrole-2-carbaldehyde;1-(Benzenesulfonyl)-4-bromo-1H-pyrrole-2-carbaldehyde;DTXSID60568030

Chemical Property of 1-(Benzenesulfonyl)-4-bromo-1H-pyrrole-2-carbaldehyde

Chemical Property:

• XLogP3: 2.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 312.94083
• Heavy Atom Count: 17
• Complexity: 373

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)S(=O)(=O)N2C=C(C=C2C=O)Br

Technology Process of 1-(Benzenesulfonyl)-4-bromo-1H-pyrrole-2-carbaldehyde

There total 6 articles about 1-(Benzenesulfonyl)-4-bromo-1H-pyrrole-2-carbaldehyde which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.0%

4-bromopyrrole-2-carboxaldehyde (931-33-9) + benzenesulfonyl chloride (98-09-9) → N-benzenesulfonyl-4-bromopyrrole-2-carbaldehyde (138371-99-0)

Guidance literature:

With tetrabutylammomium bromide; sodium hydroxide; In dichloromethane; water; at 20 ℃; for 12h;

Reference yield: 73.0%

N-benzenesulfonyl-2,4-dibromopyrrole (1229516-64-6) + formic acid ethyl ester (109-94-4) → N-benzenesulfonyl-4-bromopyrrole-2-carbaldehyde (138371-99-0)

Guidance literature:

N-benzenesulfonyl-2,4-dibromopyrrole; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h; Inert atmosphere;

formic acid ethyl ester; In tetrahydrofuran; hexane; at -78 ℃; for 1h; regioselective reaction; Inert atmosphere;

DOI:10.3987/COM-12-S(N)81

Reference yield:

N-formyldiethylamine (617-84-5) + 1-(benzenesulfonyl)-3-bromo-1H-pyrrole (1192217-75-6) → 3-bromo-1-(phenylsulfonyl)-1H-pyrrole-2-carbaldehyde (1229516-61-3) + N-benzenesulfonyl-4-bromopyrrole-2-carbaldehyde (138371-99-0)

Guidance literature:

1-(benzenesulfonyl)-3-bromo-1H-pyrrole; With n-butyllithium; diisopropylamine; In tetrahydrofuran; hexane; at -78 ℃; Inert atmosphere;

N-formyldiethylamine; In tetrahydrofuran; hexane; at -78 ℃; regioselective reaction;

DOI:10.1021/ol100810c

upstream raw materials:

4-bromopyrrole-2-carboxaldehyde

benzenesulfonyl chloride

N-formyldiethylamine

1-(benzenesulfonyl)-3-bromo-1H-pyrrole

Downstream raw materials:

t-Butyl (R,S)-N-<4-<4-(3-t-butoxycarbonyl-2,2-dimethyloxazolidin-4-yl)acetoxymethyl-1-(phenylsulfonyl)pyrrol-2-yl>-4-hydroxy-2-butynoyl>-N-methylvalinate

(R)-4-[Acetoxy-(1-benzenesulfonyl-5-{3-[((S)-1-tert-butoxycarbonyl-2-methyl-propyl)-methyl-carbamoyl]-propynoyl}-1H-pyrrol-3-yl)-methyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

t-Butyl (R,S)-N-<4-<4-(3-t-butoxycarbonyl-2,2-dimethyloxazolidin-4-yl)acetoxymethyl-1-(phenylsulfonyl)pyrrol-2-yl>-4-oxobutanoyl>-N-methylvalinate

t-Butyl (R)-4-<5-(1,3-Dioxolan-2-yl)-1-(phenylsulfonyl)pyrrol-3-yl>acetoxymethyl-2,2-dimethyl-3-oxazolidinecarboxylate