Tetrahydrothiophene → HCID 86632422, compound

HRID 1662923Notes

Reaction equation

HRID 1662923 reaction equation
[Br:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][CH:6]=1)=[O:4].[S:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1>CC(C)=O.O>[Br-:1].[O:4]=[C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][CH:6]=1)[CH2:2][S+:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

5

Reactant 2

HCID 1127TetrahydrothiopheneHCID 692722-Bromo-4'-methylacetophenone

Product 1

HCID 86632422HCID 86632422, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-bromo-4′-methylacetophenone (19.18 g, 90 mmol) in 120 mL of acetone and 4.9 mL of water at 0° C. was added tetrahydrothiophene (15.87 g, 180 mmol) dropwise. The resulting mixture was stirred at 0° C. for 1 hour before solid precipitated and was then stirred at room temperature for 1 hour. The resulting crude product was filtered through glass frit as solid and was washed by 100 mL of cold acetone. The crude product was recrystallized by 150 mL of ethanol to afford 19.8 g pure product at a yield of 73%. 1HNMR, d6-DMSO: 7.92 (d, 8.0 Hz, 2H), 7.43 (d, 8.0 Hz, 2H), 5.39 (s, 2H), 3.57 (m, 4H), 2.42 (s, 3H), 2.27 (m, 2H), 2.19 (m, 2H).

Workup

  1. customprecipitated
  2. stirringwas then stirred at room temperature for 1 hour
  3. filtrationThe resulting crude product was filtered through glass frit as solid
  4. washwas washed by 100 mL of cold acetone
  5. customThe crude product was recrystallized by 150 mL of ethanol

Sources & evidence

ORD record
ord-f0fcaf4fa17b4a0ab90018e11f29511a
Source dataset
uspto-grants-2011_10
Patent number
US08034533B2

Reaction notes

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