These common heterocyclic compound, 954-81-4, name is N-(5-Bromopentyl)phthalimide, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Formula: C13H14BrNO2
4.1.7 Synthesis of 5-N-phthalimido-1-pentyl 2′,2′,2′-trifluoroethyl sulfide 13 ( Scheme 3 ) To a solution of sodium methoxide, prepared by dissolving sodium (1.1 g, 47.82 mmol) in methanol (80 mL), a 2,2,2-trifluoroethanethiol (5 g, 43.0626 mmol) was added and left at room temperature for 1.5 h. N-(5-bromopentyl)phthalimide was added and the mixture was stirred at room temperature for 48 h. After removal of methanol the residue was dissolved in chloroform and the solution was washed with water. The organic layer was dried with MgSO4 and the solvent was removed under vacuum. The crude product was purified by column chromatography (silica gel, dichloromethane as solvent) to give pure sulfide 13 as a solid, mp = 89 C (13.88 g, 98%). 1H NMR (CDCl3): delta 1.41-1.50 (m, 2H), 1.58-1.77 (m, 4H), 2.65 (t, 2H, J = 7.20 Hz, CH2S), 3.05 (q, 2H, JH-F = 10.03 Hz, CH2CF3), 3.69 (t, 2H, J = 7.07 Hz, CH2N), 7.67-7.82 (m, 4H, arom). 19F NMR (CDCl3): delta – 65.8 (t, 3F, JH-F = 10.30 Hz). 13C NMR (CDCl3): delta 25.79, 28.11, 28.56, 32.99, 34.31 (q, JC-F = 32.31 Hz, CH2CF3), 37.69, 123.24, 125.97 (q, JC-F = 125.97 Hz, CF3CH2), 132.11, 133.97, 168.47. MS (CI, isobutane): m/z = 332.1 [M + H]+. HRMS: m/z calcd for [M + H]+ C15H17F3NO4S 332.09321, found 332.09272.
The synthetic route of N-(5-Bromopentyl)phthalimide has been constantly updated, and we look forward to future research findings.