Water → HCID 53955163, compound

HRID 342981Notes

Reaction equation

HRID 342981 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-ef251851accf48768e4de0d5c0298b08
Source dataset
uspto-grants-1999_01
Patent number
US05859283

Reaction notes

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