Реакция #85383

Уравнение реакции

hydrochloric acid

3,3,3-trifluoropropane-1-thiol

3-bromopropanoic acid

potassium hydroxide

→

oil

Выход 88.0%

3-((3,3,3-Trifluoropropyl)thio)propanoic acid

Выход 88.0%

Растворители

methanol

Условия реакции

Обработка

1. 1
   workup.ADDITIONwas added
2. 2
   Экстракцияextracted with methyl tert-butylether (MTBE, 2×10 mL)
3. 3
   КонцентрированиеThe organic layer was concentrated to dryness

Методика

A 100 mL, 3-neck round bottom flask was charged with 3-bromopropanoic acid (500 mg, 3.27 mmol) and methanol (10 mL), potassium hydroxide (KOH, 403 mg, 7.19 mmol) was added, followed by 3,3,3-trifluoropropane-1-thiol (468 mg, 3.60 mmol). The mixture was heated at 50° C. for 4 hours, after which it was acidified with 2 N hydrochloric acid and extracted with methyl tert-butylether (MTBE, 2×10 mL). The organic layer was concentrated to dryness to afford a light yellow oil (580 mg, 88%): 1H NMR (400 MHz, CDCl3) δ 2.83 (td, J=7.1, 0.9 Hz, 2H), 2.78-2.64 (m, 4H), 2.48-2.32 (m, 2H).

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