3-BROMO-N N-DIPHENYLANILINE 97 synthesis
- Product Name:3-BROMO-N N-DIPHENYLANILINE 97
- CAS Number:78600-33-6
- Molecular formula:C18H14BrN
- Molecular Weight:324.21
Yield: 93%
Reaction Conditions:
with palladium diacetate;4,5-bis(diphenylphosphino)-9,9-dimethylxanthene;sodium t-butanolate in toluene at 100; for 12 h;Inert atmosphere;chemoselective reaction;Buchwald-Hartwig Coupling;
Steps:
General procedure for the palladium-catalyzed reaction
General procedure: General procedure for the palladium-catalyzed reaction
A solution of Pd(OAc)2 (0.8 mg, 0.0036 mmol), Xantphos (2.1 mg, 0.0036 mmol), NaOtBu (51 mg, 0.53 mmol), 1-bromo-4-iodobenzene (1a) (100 mg, 0.35 mmol), and N,N-diphenylamine (2a) (72 mg, 0.43 mmol) in toluene (0.5 mL) was stirred at 100 °C for 12 h.
The reaction was quenched with H2O, and extracted with CH2Cl2 (3*3 mL).
The chemoselectivity (3aa/4aa=92/8) was measured by HPLC analysis using Inertsil ODS-3V.
The pure monoaminated product 3aa (99 mg, 86%) was obtained by flash chromatography (hexane/CH2Cl2=97/3) as a white solid.
References:
Kanazawa, Yoshinori;Yokota, Tomo;Ogasa, Hiroshi;Watanabe, Hirotaka;Hanakawa, Taisyun;Soga, Shinichi;Kawatsura, Motoi [Tetrahedron,2015,vol. 71,# 9,p. 1395 - 1402]
108-36-1
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122-39-4
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78600-33-6
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$24.00/1g