Methanethiol → HCID 54135411, compound

HRID 2256930Notes

Reaction equation

HRID 2256930 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-f263e149aa05443a9339d3ee1364d7a9
Source dataset
uspto-grants-1997_08
Patent number
US05656573

Reaction notes

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