Methanethiol → HCID 54135411, compound

HRID 266547Notes

Reaction equation

HRID 266547 reaction equation
Br[C:2]1[C:12]([O:13][CH2:14][CH2:15][O:16][CH3:17])=[C:11]([Br:18])[CH:10]=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].C(=O)([O-])[O-].[K+].[K+].[CH3:25][SH:26]>CN(C=O)C.CCOCC>[Br:18][C:11]1[CH:10]=[CH:9][C:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])=[C:2]([S:26][CH3:25])[C:12]=1[O:13][CH2:14][CH2:15][O:16][CH3:17]

Participants

6

Reactant 3

HCID 878MethanethiolHCID 11430Potassium CarbonateHCID 14851212HCID 14851212, compound

Product 1

HCID 54135411HCID 54135411, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent2×

Procedure

Ethyl 2,4-dibromo-3-(2-methoxyethoxy)benzoate(32.2 g) was stirred in DMF (80 ml) with potassium carbonate (36 g). To the resultant suspension was added a solution of methane thiol (13 ml) in DMF (20 ml). The resultant mixture was stirred overnight at room temperature. It was then diluted with ether, and the mixture washed with water, dried (anhydrous magnesium sulphate) and filtered. The filtrate was evaporated to dryness. The residue was purified by column chromatography on silica eluting with ethyl acetate and cyclohexane (1:20) which yielded ethyl 4-bromo-3-(2-methoxyethoxy)-2-methylsulphenylbenzoate (3.5 g) as an oil which was not further characterized.

Workup

  1. washthe mixture washed with water
  2. dry with materialdried (anhydrous magnesium sulphate)
  3. filtrationfiltered
  4. customThe filtrate was evaporated to dryness
  5. customThe residue was purified by column chromatography on silica eluting with ethyl acetate and cyclohexane (1:20) which

Sources & evidence

ORD record
ord-edd26f8e79b948a7a7ea71990319c499
Source dataset
uspto-grants-1997_07
Patent number
US05650533

Reaction notes

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