Thiophenol → S-Phenyl thioisobutyrate

HRID 1044431Notes

Reaction equation

HRID 1044431 reaction equation
[C:1](Cl)(=[O:5])[CH:2]([CH3:4])[CH3:3].C(N(CC)CC)C.[C:14]1([SH:20])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.CCCC(C)C.C(OCC)(=O)C>C1(C)C=CC=CC=1>[C:1](=[O:5])([S:20][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH:2]([CH3:4])[CH3:3]

Participants

6

Reactant 4

HCID 7969ThiophenolHCID 8471TriethylamineHCID 62325Isobutyryl chlorideHCID 21882781Isohexane ethyl acetate

Product 1

HCID 11105960S-Phenyl thioisobutyrateYield 72.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

Isobutanoyl chloride (528 μL, 5.0 mmol) in 15 mL toluene was added to a solution of triethylamine (0.70 mL, 5.0 mmol) and thiophenol (0.51 mL, 5.0 mmol) in 10 mL toluene. Reaction monitoring was accomplished by TLC: iso-hexane/ethyl acetate 25:1; Rf=0.47. Workup yielded 653 mg (72%) S-phenyl isobutanethioate 6 as pale yellow oil.

Workup

  1. customReaction monitoring

Sources & evidence

ORD record
ord-4c871bf2d13a4339b7c78e7168b4b04c
Source dataset
uspto-grants-2013_10
Patent number
US08563598B2

Reaction notes

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