Ethyl Bromide → Fluoresone

HRID 238587

反応式

HRID 238587 の反応式
P([O-])([O-])(O)=O.[Na+].[Na+].S([O-])([O-])=O.[Na+].[Na+].[F:14][C:15]1[CH:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[CH:17][CH:16]=1.Br[CH2:26][CH3:27]>O.CC(C)=O.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:26]([S:21]([C:18]1[CH:19]=[CH:20][C:15]([F:14])=[CH:16][CH:17]=1)(=[O:23])=[O:22])[CH3:27]

参加物

8

反応物 4

HCID 6332Ethyl BromideHCID 95884-Fluorobenzenesulfonyl chlorideHCID 24203Sodium Phosphate, DibasicHCID 24437Sodium Sulfite

生成物 1

HCID 71814Fluoresone収率 63.2%

試薬・触媒・溶媒 3

HCID 67553Tetrabutylammonium Iodide触媒HCID 180Acetone溶媒HCID 962Water溶媒2 回

反応条件

温度
60 °C

実験手順

To a solution of sodium hydrogen phosphate (14.2 g, 0.1 mol) and sodium sulfite (25.2 g, 0.2 mol) in water (200 mL) was added 4-fluoro-benzenesulfonyl chloride (19.5 g, 0.1 mol). After the mixture was stirred at 60° C. overnight, a solution of bromoethane (32.7 g, 0.3 mol) in acetone (20 mL) was added dropwise, followed by the addition of tetrabutylammonium iodide (3.7 g, 0.01 mol) in one portion. The resulting reaction mixture was stirred at room temperature for 5 days, then diluted with water (50 mL), and extracted with ethyl acetate (100 mL×3). The combined organic layers were washed with brine, dried over sodium sulfate, and concentrated in vacuo. The residue was purified by flash column chromatography (elution with 20% ethyl acetate in petroleum ether) to afford 1-ethanesulfonyl-4-fluoro-benzene (11.9 g, 63%) as a yellow oil (reference: Arnold, Leggy A. A., et al., Org. Lett, 6 (2004), 3005-3007).

後処理

  1. customThe resulting reaction mixture
  2. stirringwas stirred at room temperature for 5 days
  3. extractionextracted with ethyl acetate (100 mL×3)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash column chromatography (elution with 20% ethyl acetate in petroleum ether)

出典と根拠

ORDレコード
ord-7c0ad6e0853241309521ef6621b24da2
出典データセット
uspto-grants-2014_02
特許番号
US08642629B2

関連ノート

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