Tetrahydrothiophene → Phenacylthiophenium bromide

HRID 393502

Reaction equation

HRID 393502 reaction equation
[S:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:6]([Br:15])[C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:8].C(OCC)(=O)C>C(#N)C>[Br-:15].[CH2:6]([C:2]1[SH+:1][CH:5]=[CH:4][CH:3]=1)[C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:8]

Participants

5

Reactant 3

HCID 1127TetrahydrothiopheneHCID 6259Phenacyl bromideHCID 8857Ethyl Acetate

Product 1

HCID 86587345Phenacylthiophenium bromideYield 96.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

In 400 ml of acetonitrile was dissolved 53.2 g of tetrahydrothiophene, and to the solution was gradually added a solution containing 100 g of phenacyl bromide dissolved in 300 ml of acetonitrile. The solution was stirred at room temperature for 3 hours to deposit powder. The reaction solution was poured into 1,500 ml of ethyl acetate, and the powder deposited was collected by filtration and dried to obtain 137 g of phenacylthiophenium bromide.

Workup

  1. additionto the solution was gradually added a solution
  2. filtrationthe powder deposited was collected by filtration
  3. customdried

Sources & evidence

ORD record
ord-f61801c6588d44f9bdc17d5abe309810
Source dataset
uspto-grants-2004_10
Patent number
US06808862B2

Linked notes

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