Benzyl Bromide → O-Benzyl methanesulfonothioate

HRID 650860Notes

Reaction equation

HRID 650860 reaction equation
[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]

Participants

4

Reactant 2

HCID 7498Benzyl BromideHCID 23688755Methanesulfonothioic acid, sodium salt

Product 1

HCID 53443207O-Benzyl methanesulfonothioate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-28b85e9ff2854277afa4afd3f0e9a496
Source dataset
uspto-grants-2001_08
Patent number
US06277617B1

Reaction notes

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