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

HRID 2242297Notes

Reaction equation

HRID 2242297 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-828adebd7848492288fb42db4e12c011
Source dataset
uspto-grants-2010_03
Patent number
US07671082B2

Reaction notes

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