Water → HCID 23157940, compound

HRID 1360216Notes

Reaction equation

HRID 1360216 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:9](=N)[O:10][CH2:11][CH3:12])[CH:5]=[CH:6][C:7]=1[SH:8].O.S(=O)(=O)(O)[OH:16]>C(O)C.[Zn]>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[SH:8])[C:9]([O:10][CH2:11][CH3:12])=[O:16]

Participants

6

Reactant 3

HCID 962WaterHCID 1118Sulfuric AcidHCID 135618202HCID 135618202, compound

Product 1

HCID 23157940HCID 23157940, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

Ethyl 3-bromo-4-mercaptobenzenecarboximidate (3.00 g) was dissolved in ethanol (100 ml), and water (10 ml) and then concentrated sulfuric acid (10 ml) were added dropwise thereto at 0° C. and stirred overnight at room temperature. Zinc (1 g) was added to the reaction system and the resulting mixture was stirred at room temperature for 2 hours to induce the production of a monomer. After the zinc powder was removed by filtration through Celite, the ethanol was distilled off under reduced pressure, followed by extraction with ethyl acetate, and the organic layer was washed with water (×4). The organic layer was dried over anhydrous sodium sulfate and then concentrated to obtain ethyl 3-bromo-4-mercaptobenzoate (2.58 g) as a light-yellow solid.

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 2 hours
  2. customAfter the zinc powder was removed by filtration through Celite
  3. distillationthe ethanol was distilled off under reduced pressure
  4. extractionfollowed by extraction with ethyl acetate
  5. washthe organic layer was washed with water (×4)
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-98c495470ab34b439df8ab4ca1571ba3
Source dataset
uspto-grants-2011_02
Patent number
US07879843B2

Reaction notes

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