ChemicalBook CAS DataBase List N,N-Diphenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

N,N-Diphenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline synthesis

14synthesis methods

Product Name:N,N-Diphenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline
CAS Number:267221-88-5
Molecular formula:C24H26BNO2
Molecular Weight:371.28

61676-62-8 Synthesis

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

61676-62-8
321 suppliers
$10.00/5g

N,N-Diphenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

267221-88-5
103 suppliers
$10.00/250mg

Yield: 72.8%

Reaction Conditions:

Stage #1:4-N,N-diphenylamino-1-bromobenzene with n-butyllithium in tetrahydrofuran at -78 - -50;Cooling with acetone-dry ice;
Stage #2:2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane in tetrahydrofuran at -78 - 20; for 15 h;Cooling with acetone-dry ice;

Steps:

11 Synthesis of N,N-diphenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline
Example 11 Synthesis of N,N-diphenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline n-Butyllithium was added dropwise via syringe to a -78° C. (acetone-dry ice cooling bath) solution of 4-bromo-N,N-diphenylaniline (24 g, 0.074 mole) in 175 ml dry THF. Stirring was continued at -78° C. for an hour and then at -50° C. for an hour. The mixture was cooled to -78° C. and 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (17.22 g, 0.0925 mole) added via syringe in one portion. The temperature was maintained at -78° C. for three hours. The cooling bath was removed and the reaction left to warm to room temperature while standing for 12 hours. The reaction mixture was poured into saturated ammonium acetate and extracted with ether. The ether layer was dried over magnesium sulfate and concentrated to give a viscous oil. Purification by column chromatography (silica gel eluding with hexane:toluene mixtures of increasing gradient from 100% hexane to 40% hexane) gave N,N-diphenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline as an oil (19.9 g, 72.8% yield), which slowly crystallized to a solid on standing.

References:

3M Innovative Properties Company US7094902, 2006, B2 Location in patent:Page/Page column 92-93

36809-26-4 Synthesis