Hydrochloric Acid → 9,10-Diphenylanthracene-2-boronic Acid

HRID 1513620Notes

Reaction equation

Br[C:2]1[CH:15]=[CH:14][C:13]2[C:4](=[C:5]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:6]3[C:11]([C:12]=2[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH:3]=1.C([Li])CCC.C[O:34][B:35](OC)[O:36]C.Cl>C1COCC1>[C:16]1([C:12]2[C:11]3[C:6]([C:5]([C:4]4[CH:13]=[CH:14][CH:15]=[CH:2][CH:3]=4)=[C:22]4[C:23]=2[CH:24]=[C:25]([B:35]([OH:36])[OH:34])[CH:26]=[CH:27]4)=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

Conditions

Temperature: -78 °C

Procedure

Dehydrated THF 50 mL was added to 3.5 g (8.6 mmol) of 2-bromo-9,10-diphenylanthracene under argon atmosphere and cooled down to −78° C., and 6.0 mL of n-butyllithium (in 1.6M hexane) was dropwise added thereto. After stirring at −78° C. for one hour, the temperature was elevated up to 0° C. The solution was cooled down again to −78° C., and 2.9 mL (26 mmol) of trimethoxyborane was dropwise added thereto. The solution was stirred at −78° C. for one hour and then stirred at room temperature for 2 hours. 10% HCl 50 mL was added thereto, and the solution was stirred for one hour and then filtered. The solid matter thus obtained was washed with toluene to obtain 2.6 g (yield: 80%) of 9,10-diphenylanthracene-2-boronic acid.

Workup

customwas elevated up to 0° C
temperatureThe solution was cooled down again to −78° C.
stirringThe solution was stirred at −78° C. for one hour
stirringstirred at room temperature for 2 hours
stirringthe solution was stirred for one hour
filtrationfiltered
customThe solid matter thus obtained
washwas washed with toluene

Sources & evidence

ORD record: ord-e523fa1814a4426ab74732ff586d33df
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08217570B2

Reaction notes

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