반응 #334376

반응 방정식

5-iodo-1-naphthalenecarboxylic acid methyl ester

trifluoromethyl iodide

→

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

수율 60.4%

용매

pyridine

반응 조건

후처리

1. 1
   기타prepared
2. 2
   온도cooled to room temperature
3. 3
   여과The mixture was filtered
4. 4
   기타to remove insoluble material
5. 5
   세척The filtrate was washed with 1N aqueous HCl, water and brine
6. 6
   건조dried (MgSO4)
7. 7
   농축concentrated to dryness
8. 8
   기타The residue was crystallized from methanol

실험 절차

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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