Hydrochloric Acid → HCID 86699218, compound

HRID 532606Notes

Reaction equation

HRID 532606 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]2[C:6](=[O:9])[CH2:7][CH2:8][C:2]1=2.[H-].[Na+].C1([O:18][C:19](=O)[C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([Br:26])[CH:21]=2)C=CC=CC=1.Cl>C1COCC1.C(OCC)(=O)C.O>[Br:26][C:22]1[CH:21]=[C:20]([CH:25]=[CH:24][CH:23]=1)[C:19]([CH:7]1[CH2:8][C:2]2[S:1][CH:5]=[CH:4][C:3]=2[C:6]1=[O:9])=[O:18]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 522791HCID 522791, compoundHCID 19586324H,5H,6H-cyclopenta[b]thiophen-4-one

Product 1

HCID 86699218HCID 86699218, compoundYield 58%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

5,6-Dihydro-cyclopenta[b]thiophen-4-one (2.1 g, 15.0 mmol) in 15 mL of THF was treated with NaH (60 percent, 1.5 g, 36 mmol). After the addition of 3-Bromo-benzoic acid phenyl ester, the reaction mixture was heated at 100° C. for 8 hr. The solution was cooled to room temperature and poured into water. The resulting mixture was acidified with concentrated HCl and was added with ethyl acetate (80 mL). The organic layer was collected, brined, dried over MgSO4(s), and concentrated under reduced pressure. The resultant precipitate was collected and recrystallized from ethanol to provide the corresponding 5-(3-Bromo-benzoyl)-5,6-dihydro-cyclopenta[b]thiophen-4-one (2.5 g, 8.2 mmol) as brown solid in 58% yield.

Workup

  1. temperatureThe solution was cooled to room temperature
  2. customThe organic layer was collected
  3. dry with materialdried over MgSO4(s)
  4. concentrationconcentrated under reduced pressure
  5. customThe resultant precipitate was collected
  6. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-d76088d08af14ade9aa979d02610baa5
Source dataset
uspto-grants-2014_10
Patent number
US08853207B2

Reaction notes

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