Water → HCID 53955163, compound

HRID 266539Notes

Reaction equation

HRID 266539 reaction equation
[CH2:1]([SH:3])[CH3:2].[Br:4][C:5]1[C:15]([O:16][CH3:17])=[C:14](Br)[CH:13]=[CH:12][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[Br:4][C:5]1[C:15]([O:16][CH3:17])=[C:14]([S:3][CH2:1][CH3:2])[CH:13]=[CH:12][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8]

Participants

6

Reactant 4

HCID 962WaterHCID 6343EthanethiolHCID 11430Potassium CarbonateHCID 54096575HCID 54096575, compound

Product 1

HCID 53955163HCID 53955163, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Ethyl mercaptan (5 ml) was added to a suspension of ethyl 2,4-dibromo-3-methoxybenzoate (10.0 g) and potassium carbonate (9.0 g) in dimethylformamide (DMF). The mixture was stirred at room temperature for 48 hours, water was added and the mixture was extracted with ether, washed with water, dried (MgSO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by medium pressure chromatography eluted with a mixture of ethyl acetate and cyclohexane to give ethyl 2-bromo-4-(ethylsulphenyl)-3-methoxybenzoate (3.98 g) as an oil NMR (CDCl3) 1.35(m,6H) 2.9(q,2H) 3.8(s,3H) 4.4(q,2H) 7.1-7.4(m,2H).

Workup

  1. extractionthe mixture was extracted with 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 medium pressure chromatography
  7. washeluted with a mixture of ethyl acetate and cyclohexane

Sources & evidence

ORD record
ord-b2e07e56163247208a53021846ba63ba
Source dataset
uspto-grants-1997_07
Patent number
US05650533

Reaction notes

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