Methanethiol → HCID 54477101, compound

HRID 343014Notes

Reaction equation

HRID 343014 reaction equation
[CH3:1][SH:2].Br[C:4]1[C:14]([O:15][CH3:16])=[C:13]([Br:17])[CH:12]=[CH:11][C:5]=1[C:6]([O:8][CH2:9][CH3:10])=[O:7].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[Br:17][C:13]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[C:4]([S:2][CH3:1])[C:14]=1[O:15][CH3:16]

Participants

6

Reactant 4

HCID 878MethanethiolHCID 962WaterHCID 11430Potassium CarbonateHCID 54096575HCID 54096575, compound

Product 1

HCID 54477101HCID 54477101, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of methanethiol (47 ml) in dimethyl formamide was added to a mixture of ethyl 2,4-dibromo-3-methoxybenzoate (105 g) and potassium carbonate (131 g) in dimethyl formamide and the resultant suspension was stirred at room temperature overnight. Water was added and the mixture was extracted into ether, washed with water, dried (MgSO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by column chromatography eluted with a mixture of ethyl acetate and cyclohexane to give as the minor component ethyl 4-bromo-3-methoxy-2-(methylsulphenyl)-benzoate (4.5 g) as a white solid, NMR (CDCl3) 1.5(t,3H), 2.6(s,3H), 4.05(s,3H), 4.5(q,2H), 7.35 (m,2H).

Workup

  1. extractionthe mixture was extracted into ether
  2. washwashed with water
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customThe filtrate was evaporated to dryness
  6. customthe residue was purified by column chromatography
  7. washeluted with a mixture of ethyl acetate and cyclohexane

Sources & evidence

ORD record
ord-a0739e5fc56c453f87bcf17bd7821914
Source dataset
uspto-grants-1999_01
Patent number
US05859283

Reaction notes

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