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ChemicalBook CAS DataBase List N-(4-bromophenyl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9-dimethyl-9H-fluoren-2-amine
313050-71-4

N-(4-bromophenyl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9-dimethyl-9H-fluoren-2-amine synthesis

7synthesis methods
165320-27-4 Synthesis
N,N-Bis(9,9-dimethyl-9H-fluoren-2-yl)aniline

165320-27-4
29 suppliers
$74.00/200mg

-

Yield:313050-71-4 94%

Reaction Conditions:

with N-Bromosuccinimide in tetrahydrofuran at 0; for 3 h;

Steps:

N-(4-bromophenyl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9-dimethyl-9H-fluoren-2-amine (2)
1 (719 mg, 1.51 mmol) was dissolved in 20 ml THF and the solution was cooled to 0 C, N-bromosuccinimide (274 mg, 1.51 mmol) was added in one portion. The reaction mixture was maintained at this temperature and stirred for 3h, then quenched with Na2SO3 (aq) and extracted with CH2Cl2. The combined organic layer was washed with brine, dried with Na2SO4. Silica gel column chromatography using CHCl3/hexane (v/v = 1:3) as eluent gave product as yellow powder (790 mg), yield 94%. 1H NMR (400 MHz, CDCl3) δ = 7.65 (s, 1H), 7.63 (s, 1H), 7.60 (s, 1H), 7.58 (s, 1H), 7.42 - 7.25 (m, 8H), 7.19 (d, J = 1.3 Hz, 2H), 7.06 (d, J = 8.6 Hz, 4H), 1.45 - 1.36 (m, 12H). MS calcd: m/z 555.16 ([M+]), TOF-MS found 555.5070 ([M+]).

References:

Liu, Quan;Kong, Fan-Tai;Okujima, Tetsuo;Yamada, Hiroko;Dai, Song-Yuan;Uno, Hidemitsu;Ono, Noboru;You, Xiao-Zeng;Shen, Zhen [Tetrahedron Letters,2012,vol. 53,# 26,p. 3264 - 3267] Location in patent:supporting information; experimental part

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