Реакция #577203

Уравнение реакции

4-ethynylaniline

triethylamine

4-ethynylaniline

1,4-Diiodobenzene

→

desired product

4-(4-Iodophenylethynyl)Aniline

Растворители

THF

Условия реакции

Обработка

1. 1
   ДругоеThe tube was capped

Методика

1,4-Diiodobenzene (4.95 g, 1.0 mmol), bis(triphenylphosphine)palladium(II) dichloride (0.070 g, 0.10 mmol), copper(I) iodide (0.019 g, 0.10 mmol), triethylamine (5 mL), THF (10 mL) and 4-ethynylaniline 0.585 g, 5.00 mmol) were used following the general procedure for couplings. For the synthesis of 4-ethynylaniline, please see Tour et al. Chem. Eur. J. 2001, vol. 7, pp. 5118-5134 incorporated herein by reference. The tube was capped and stirred room temperature for 12 h. Flash column chromatography (CH2Cl2—hexanes as eluent) afforded the desired product as light yellow needles (1.13 g, 71% yield). IR (KBr) 3441, 3356, 2210, 1612, 1515, 1281, 1135, 1003, 842, 811, 512 cm−1. 1H NMR (400 MHz, CDCl3) δ7.650 (m, AA′ part of AA‘XX’ pattern, J=8.7, 2.4, 1.8, 0.7 Hz, 2H), 7.324 (m, XX′ part of AA′XX′ pattern, J=8.7, 2.4, 1.8, 0.7 Hz, 2H), 7.208 (m, AA′ part of AA′XX′ pattern, J=8.6, 2.4, 1.8, 0.6 Hz, 2H), 6.630 (m, XX′ part of AA′XX′ pattern, J=8.6, 2.4, 1.8, 0.6 Hz, 2H), 3.833 (s, 2H). 13C NMR (100 MHz, CDCl3) δ 147.05, 137.60, 133.20, 133.07, 123.67, 114.95, 112.39, 93.45, 91.83, 86.69.

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