Benzyl Bromide → O-Benzyl methanesulfonothioate

HRID 650860ノート

反応式

HRID 650860 の反応式
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:9][S:10](=[S:13])([O-:12])=[O:11].[Na+]>CCO>[CH3:9][S:10](=[S:13])([O:12][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:11]

参加物

4

反応物 2

HCID 7498Benzyl BromideHCID 23688755Methanesulfonothioic acid, sodium salt

生成物 1

HCID 53443207O-Benzyl methanesulfonothioate

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

Benzyl bromide (9.07 g, 0.053 mol) was slowly added to a suspension of sodium methanethiosulfonate (7.10 g, 0.0530 mol) in absolute EtOH (100 mL) and the reaction mixture was heated at reflux overnight. The reaction mixture was cooled with an ice bath and the solid (sodium bromide and sodium methanethiosulfonate) was filtered off. The filtrate was concentrated to give a crude product which was mainly the desired product. Pure product was obtained by flash chromatography on silica gel with EtOAc-hexanes (1:6) (7.92 g, 74%). The product was further purified by recrystallization from absolute ethanol. mp 39.5-40.2° C. (lit. 40-42.5° C.) IR (KBr): 3089, 3068, 3017, 3000, 2981, 2936, 2918, 1602, 1582, 1496, 1305, 1131, 960, 771, 741, 702 cm−1. 1H NMR (200 MHz, CDCl3): δ 7.38 (m, 5H, phenyl), 4.38 (s, 2H, SCH2), 2.91 (s, 3H, CH3SO2). 13C NMR (50 MHz, CDCl3): δ 135.12, 129.14, 129.03, 128.26, 51.09, 40.79.

後処理

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux overnight
  3. temperatureThe reaction mixture was cooled with an ice bath
  4. filtrationthe solid (sodium bromide and sodium methanethiosulfonate) was filtered off
  5. concentrationThe filtrate was concentrated
  6. customto give a crude product which

出典と根拠

ORDレコード
ord-28b85e9ff2854277afa4afd3f0e9a496
出典データセット
uspto-grants-2001_08
特許番号
US06277617B1

反応ノート

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