BIS(4-BROMOPHENYL)AMINE synthesis
- Product Name:BIS(4-BROMOPHENYL)AMINE
- CAS Number:16292-17-4
- Molecular formula:C12H9Br2N
- Molecular Weight:327.01
Yield:16292-17-4 68%
Reaction Conditions:
with palladium diacetate;sodium t-butanolate in toluene at 150; for 0.5 h;Microwave irradiation;Buchwald-Hartwig Coupling;
Steps:
Synthesis of bis(bromophenyl)amine (3):
To a flame dried 35 mL microwave vial with a teflon cap, 16 mL of anhydrous toluene wasadded followed by 3.18 g (33.1 mmol) of sodium tert-butoxide then 2.6 mL (23 mmol) of 2-bromoaniline (1) and 3.0 mL (23 mmol) of 2-bromoiodobenzene (2) dropwise and stirred.The ligand DPEPhos, 103 mg (0.190 mmol), and 29.8 mg (0.133 mmol) Pd(OAc)2 wereadded then heated 30 minutes at 150 °C in a microwave reactor. The product was extractedwith 3 x 35 mL of dichloromethane and the combined organic layer was washed with water(3 x 150mL). The organic layer was dried over magnesium sulfate and concentrated invacuuo. The resulting product was recrystallized from ethanol to yield white or gray needlelikecrystals in 68 % yield.MP 59.8-60.7 °C 1H-NMR (400 MHz, CDCl3) δ: 7.58 (dd, J = 8.0 Hz, 1.6 Hz, 2H), 7.30 (dd,J = 8.0 Hz, 1.6 Hz, 2H), 7.22 (td, J = 8.4 Hz, 1.2 Hz, 2H), 6.84 (td, J = 7.6 Hz, 2.0 Hz, 2H),6.44 (s, 1H) 13C-NMR (100 MHz, CDCl3) δ: 140.13, 133.39, 128.23, 122.67, 118.08, 114.38HRMS (EI) calc. for C12H9Br2N 324.9102, found 324.9094 UV-Vis (CH2Cl2) λ max (ε, cm-1M-1) 287 (39000)
References:
Berger, Kristen E.;McCormick, Grant M.;Jaye, Joseph A.;Rozeske, Christina M.;Fort, Eric H. [Molecules,2018,vol. 23,# 11,art. no. 2867] Location in patent:supporting information
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