Water → 4-(Tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

HRID 446638Notes

Reaction equation

BrC1C=CC([N:8]([C:15]2[C:24]3[C:19](=CC=CC=3)[CH:18]=[CH:17][CH:16]=2)C2C=CC=CC=2)=CC=1.C([Li])CCC.C(O[B:34]1[O:38][C:37]([CH3:40])([CH3:39])[C:36]([CH3:42])([CH3:41])[O:35]1)(C)C.O>C1COCC1.C(Cl)(Cl)Cl>[CH3:41][C:36]1([CH3:42])[C:37]([CH3:40])([CH3:39])[O:38][B:34]([C:18]2[CH:17]=[CH:16][C:15]([NH2:8])=[CH:24][CH:19]=2)[O:35]1

Participants

Conditions

Temperature: -78 °C

Procedure

3.7 g (10 mmol) of (4-bromophenyl)naphthalen-1-yl-phenylamine was dissolved in 100 ml of THF and cooled to −78° C. 4.8 ml (12 mmol) of 2.5M n-butyllithium was added slowly to the THF solution and maintained at the same temperature as above for an hour to allow reaction. 2.2 g (12 mmol) of 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane was added to the reactant solution, maintained at the same temperature as above for an hour to allow reaction, heated to room temperature (RT) and stirred for 24 hours. Water was added to end the reaction, and 300 ml of chloroform was added. The resulting organic layer was washed with 200 ml of water and dried with anhydride magnesium sulfate. 3.4 g of Naphthalen-1-yl-phenyl[4-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)phenylamine (intermediate A) was obtained through silica chromatography with a yield of 81%.

Workup

temperaturemaintained at the same temperature as above for an hour
customreaction
temperaturemaintained at the same temperature as above for an hour
customreaction
temperatureheated to room temperature (RT)
additionwas added
washThe resulting organic layer was washed with 200 ml of water
dry with materialdried with anhydride magnesium sulfate

Sources & evidence

ORD record: ord-8245b49ba6054495b814f225268dd7ea
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08481174B2

Reaction notes

Loading…