Ethyl Bromide → Fluoresone

HRID 238587

반응식

HRID 238587 반응식
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]

참가 물질

8

반응물 4

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

생성물 1

HCID 71814Fluoresone수율 63.2%

시약·촉매·용매 3

HCID 67553Tetrabutylammonium Iodide촉매HCID 180Acetone용매HCID 962Water용매2회

반응 조건

온도
60 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-7c0ad6e0853241309521ef6621b24da2
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08642629B2

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