Sodium Iodide → 3-bromo-6-iodo-4H-thieno[3,2-b]pyrrole-5-carboxylic acid methyl ester

HRID 716540

反応式

HRID 716540 の反応式
ClN1C(=O)CCC1=O.[I-:9].[Na+].[CH3:11][O:12][C:13]([C:15]1[NH:19][C:18]2[C:20]([Br:23])=[CH:21][S:22][C:17]=2[CH:16]=1)=[O:14].[O-]S([O-])=O.[Na+].[Na+]>CC(C)=O>[CH3:11][O:12][C:13]([C:15]1[NH:19][C:18]2[C:20]([Br:23])=[CH:21][S:22][C:17]=2[C:16]=1[I:9])=[O:14]

参加物

6

反応物 4

HCID 5238Sodium IodideHCID 24437Sodium SulfiteHCID 31398ChlorosuccinimideHCID 44118324Methyl 3-bromo-4H-thieno[3,2-b]pyrrole-5-carboxylate

生成物 1

HCID 583104013-bromo-6-iodo-4H-thieno[3,2-b]pyrrole-5-carboxylic acid methyl ester収率 68%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒3 回

実験手順

To a solution of N-chlorosuccinimide (12 mmol) in acetone (25 mL) was added dropwise a solution of sodium iodide (12 mmol) in acetone (80 mL). 3-Bromo-4H-thieno[3,2-b]pyrrole-5-carboxylic acid methyl ester (10 mmol) in acetone (80 mL) was then added portionwise into the reaction mixture. After 1 hr of stirring, the reaction was poured into a solution of Na2SO3 10% and extracted with AcOEt. Organic phases were washed with brine, dried over Na2SO4, filtered, and evaporated. The residue was purified by silica gel chromatography to give compound 69 as a yellowish solid in 68% yield. 1H NMR (CDCl3, 400 MHz) δ (ppm) 3.96 (s, 3H), 7.26 (s, 1H), 9.22 (s, 1H).

後処理

  1. extractionextracted with AcOEt
  2. washOrganic phases were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by silica gel chromatography

出典と根拠

ORDレコード
ord-3320e1ee71794558af04f6a3ac3f6a07
出典データセット
uspto-grants-2015_11
特許番号
US09187496B2

関連ノート

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