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

HRID 1690821Notes

Reaction equation

HRID 1690821 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-4985b6c5756c4f13ac98f992f7dc5ac0
Source dataset
uspto-grants-2012_04
Patent number
US08153683B2

Reaction notes

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