ChemicalBook CAS DataBase List (4-TERT-BUTYL-PHENYL)-PHENYL-AMINE

(4-TERT-BUTYL-PHENYL)-PHENYL-AMINE synthesis

15synthesis methods

Product Name:(4-TERT-BUTYL-PHENYL)-PHENYL-AMINE
CAS Number:4496-49-5
Molecular formula:C16H19N
Molecular Weight:225.33

59970-38-6
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62-53-3 Synthesis

62-53-3
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4496-49-5
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Yield: 99%

Reaction Conditions:

with water;potassium carbonate;palladium diacetate;dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine in tert-butyl alcohol at 110; for 4 h;Product distribution / selectivity;Inert atmosphere;

Steps:

13
EXAMPLE THIRTEEN: Experimental Procedures for Reactions Described in Table 4, Figure 8; General Procedure Using the Precatalysts An oven-dried test tube, which was equipped with a magnetic stir bar and fitted with a teflon septum, was charged with the precatalyst (1 mol%), ligand (1 mol%), 4-t- butylphenyl methanesulfonate (0.5 mmol, 114 mg), and K₂CO₃ (97 mg, 0.7 mmol). The vessel was evacuated and backfilled with argon (this process was repeated a total of 3 times) and then the aniline (55 μL, 0.6 mmol) and tert-butanol (6 mL) were added via syringe. The solution was heated to 110 ⁰C for 4 h, cooled to room temperature, diluted with Ethyl acetate, and washed with water. Dodecane was then added as an internal standard and the reaction was analyzed by GC.General Procedure for Water-Mediated Catalyst PreactivationAn oven-dried test tube, which was equipped with a magnetic stir bar and fitted with a teflon septum, was charged with Pd(OAc)₂ (1 mol%) and ligand (3 mol%). The vessel was evacuated and backfilled with argon (this process was repeated a total of 3 times) and the tert-butanol (1 mL) and degassed H₂O (8 mol%) were added via syringe. After addition of the water, the solution was heated to 110 ⁰C for 1 min.A second oven-dried test tube, which was equipped with a magnetic stir bar and fitted with a Teflon septum, was charged with 4-t-butylphenyl methanesulfonate (0.5 mmol, 114 mg) and K₂CO₃ (97 mg, 0.7 mmol). The vessel was evacuated and backfilled with argon (this process was repeated a total of 3 times) and then the aniline (55 μL, 0.6 mmol) and tert-butanol (5 mL) were added via syringe and the activated catalyst solution was transferred from the first reaction vessel into the second via cannula. The solution was heated to 110 ⁰C for 4 h, cooled to room temperature, diluted with Ethyl acetate, and washed with water. Dodecane was then added as an internal standard and the reaction was analyzed by GC.

References:

MASSACHUSETTS INSTITUTE OF TECHNOLOGY WO2009/76622, 2009, A2 Location in patent:Page/Page column 123-124