Methanethiol → HCID 54135411, compound

HRID 342989Notes

Reaction equation

HRID 342989 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-7c1bcd28adc24f4ea6e4ded4a6ec5bd9
Source dataset
uspto-grants-1999_01
Patent number
US05859283

Reaction notes

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