Реакция #334376

Уравнение реакции

5-iodo-1-naphthalenecarboxylic acid methyl ester

trifluoromethyl iodide

→

5-(trifluoromethyl)-1-naphthalenecarboxylic acid methyl ester

Выход 60.4%

Растворители

pyridine

Условия реакции

Обработка

1. 1
   Другоеprepared
2. 2
   Температураcooled to room temperature
3. 3
   ФильтрацияThe mixture was filtered
4. 4
   Другоеto remove insoluble material
5. 5
   ПромывкаThe filtrate was washed with 1N aqueous HCl, water and brine
6. 6
   Сушкаdried (MgSO4)
7. 7
   Концентрированиеconcentrated to dryness
8. 8
   ДругоеThe residue was crystallized from methanol

Методика

A mixture of 5-iodo-1-naphthalenecarboxylic acid methyl ester [8.8 g, 28 mmoles, described by C. Seer and R. School, Justus Leibigs Ann. Chem., 398, 82 (1913)], trifluoromethyl iodide (12 g, 61.2 mmoles), freshly prepared copper powder (5.7 g, prepared according to the procedure of R. Q. Brewster and T. Groening, "Organic Syntheses", Coll. Vol. II, John Wiley and Sons, New York, N.Y., U.S.A., 1948, p. 445) and pyridine (45 ml) was charged into a stainless steel autoclave. The vessel was shaken and heated at 130° C. for 24 hr and cooled to room temperature. The mixture was filtered to remove insoluble material. The filtrate was washed with 1N aqueous HCl, water and brine, dried (MgSO4) and concentrated to dryness. The residue was crystallized from methanol to give 4.3 g of 5-(trifluoromethyl)-1-naphthalenecarboxylic acid methyl ester, NMR (CDCl3) δ 4.0 (s, 3H), 8.0 (m, 6H).

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