Tetrahydrothiophene → Thiophenium, 1-[2-(1,1-dimethylethoxy)-2-oxoethyl]tetrahydro-, bromide (1:1)

HRID 2222733Notes

Reaction equation

HRID 2222733 reaction equation
[Br:1][CH2:2][C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].[S:10]1[CH2:14][CH2:13][CH2:12][CH2:11]1>CC(C)=O>[Br-:1].[C:6]([O:5][C:3](=[O:4])[CH2:2][S+:10]1[CH2:14][CH2:13][CH2:12][CH2:11]1)([CH3:9])([CH3:8])[CH3:7]

Participants

4

Reactant 2

HCID 1127TetrahydrothiopheneHCID 79177tert-Butyl bromoacetate

Product 1

HCID 85844044Thiophenium, 1-[2-(1,1-dimethylethoxy)-2-oxoethyl]tetrahydro-, bromide (1:1)Yield 92.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
20 °C

Procedure

Add t-butyl bromoacetate (2.44 L, 16.52 mole, 1 eq) to a solution of tetrahydrothiophene (2.19 L, 24.8 mole, 1.5 eq) in acetone (11.38 L), in a 22 L flask over 30-60 minutes while maintaining the temperature between 15-25° C. using a water bath. Stir the reaction for 22 hours and assay a sample by 1H NMR to confirm the completion of the reaction. Filter the precipitate, wash with acetone (2 L), and vacuum dry for 3 days at 28-33° C. to give 4.328 Kg (92.5% yield) of the title compound.

Workup

  1. customthe reaction for 22 hours
  2. customthe completion of the reaction
  3. filtrationFilter the precipitate
  4. washwash with acetone (2 L), and vacuum
  5. customdry for 3 days at 28-33° C.

Sources & evidence

ORD record
ord-bde3385fd508472aa0b8b93823d8c489
Source dataset
uspto-grants-2008_05
Patent number
US07371872B2

Reaction notes

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