2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane → Bis(biphenyl-4-yl)[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl]amine

HRID 1907079Notes

Reaction equation

[C:1]1([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:6]=[CH:5][C:4]([N:7]([C:20]2[CH:25]=[CH:24][C:23](Br)=[CH:22][CH:21]=2)[C:8]2[CH:13]=[CH:12][C:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:10][CH:9]=2)=[CH:3][CH:2]=1.[Li]CCCC.C(O[B:42]1[O:46][C:45]([CH3:48])([CH3:47])[C:44]([CH3:50])([CH3:49])[O:43]1)(C)C>C1COCC1>[C:1]1([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:6]=[CH:5][C:4]([N:7]([C:20]2[CH:25]=[CH:24][C:23]([B:42]3[O:46][C:45]([CH3:48])([CH3:47])[C:44]([CH3:50])([CH3:49])[O:43]3)=[CH:22][CH:21]=2)[C:8]2[CH:13]=[CH:12][C:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:10][CH:9]=2)=[CH:3][CH:2]=1

Participants

Conditions

Temperature: -78 °C

Procedure

N-(biphenyl-4-yl)-N-(4-bromophenyl)biphenyl-4-amine (56 g, 0.117 mol) was introduced into a 2 L RBF, and dissolved in THF (600 ml). Then, the temperature was maintained at −78° C. for about 30 minutes. Then, n-BuLi (1.6M in Hex) (90 ml, 0.141 mol) was slowly added thereto. After 1 hour, 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (26.2 g, 0.141 mol) was added thereto, followed by heat-stirring at room temperature for 12 hours. After the reaction was completed, the resultant solution was sufficiently washed with distilled water and Brain, and purified through column chromatography to obtain N-(biphenyl-4-yl)-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)biphenyl-4-amine (white solid, 20 g, yield 33%).

Workup

washthe resultant solution was sufficiently washed with distilled water and Brain
custompurified through column chromatography

Sources & evidence

ORD record: ord-4008f93fd0394ed8bc00a2560f7fed81
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08597802B2

Reaction notes

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