Water → Methyl 4-bromo-2-((methylthio)methyl)benzoate

HRID 2393013Notes

Reaction equation

HRID 2393013 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([CH2:12]Br)[CH:3]=1.[CH3:14][S-:15].[Na+].O>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([CH2:12][S:15][CH3:14])[CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4378561Sodium methanethiolateHCID 22031079Methyl 4-bromo-2-(bromomethyl)benzoate

Product 1

HCID 18978023Methyl 4-bromo-2-((methylthio)methyl)benzoateYield 41.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of methyl 4-bromo-2-(bromomethyl)benzoate (12 g) and sodium thiomethoxide (2.5 g) in toluene was stirred at 100° C. for 2 hours. The mixture was then cooled, poured into water and extracted with ethyl acetate. The organic layer was separated, washed with brine, dried (anhydrous sodium sulphate) and evaporated to afford a brown oil which was purified by column chromatography on silica gel giving methyl 4-bromo-2-(methylsulphenylmethyl)benzoate (4.1 g) as white crystals, m.p. 79.3° C.

Workup

  1. temperatureThe mixture was then cooled
  2. extractionextracted with ethyl acetate
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried (anhydrous sodium sulphate)
  6. customevaporated
  7. customto afford a brown oil which
  8. customwas purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-18e7dd901f034741b338d2d81b937741
Source dataset
uspto-grants-1998_09
Patent number
US05804532

Reaction notes

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