SCOPUS 정보 검색 플랫폼

Volumn , Issue 6, 2007, Pages 980-982

Iodine-magnesium exchange on unprotected imidazoles in the presence of LiCl

Author keywords

Exchange reaction; Heterocycles; Imidazole; Magnesium; Organometallic reagents

Indexed keywords

IMIDAZOLE DERIVATIVE; IODINE; LITHIUM CLORIDE; MAGNESIUM; ORGANOMETALLIC COMPOUND; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; ELECTROPHILIC STRESS; STOICHIOMETRY;

EID: 34247114178 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2007-970784 Document Type: Article

Times cited : (13)

References (9)

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2
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4
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9
- 34247176051
- Typical Procedure for the Synthesis of 4-Iodo-5-(methylsulfanyl)-1H-imidazole (3i) 4,5-diiodo-1H-imidazole (1b, 640 mg, 2.00 mmol) was placed in a dry and argon-flushed Schlenk tube equipped with a magnetic stirring bar and a septum. A solution of LiCl in THF (0.5 M, 4.0 mL, 2.0 mmol, 1.0 equiv) was added and after stirring 5 min at r.t, the resulting slurry was cooled to -20°C and MeMgCl (3.0 M in THF, 0.7 mL, 2.0 mmol, 1.0 equiv) was added dropwise. After completion of the addition, the mixture was stirred at -20°C for further 20 min. Then, i-PrMgCl·LiCl (1.3 M in THF, 1.7 mL, 2.2 mmol, 1.1 equiv) was added slowly and the resulting mixture was allowed to warm to r.t. The exchange reaction was monitored by TLC (samples quenched with MeOH, silica plates; CH2Cl2-MeOH, 19:1) versus the starting material and was usually complete after 45 min. The resulting slurry was cooled to -20°C and (5)-methyl methanesulfonothioat
- 2-MeOH, 19:1) afforded 4-iodo-5-(methylsulfanyl)-1H-imidazole (3i) as colorless solid (mp 126.1-128.4°C).

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