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

HRID 571585Notes

Reaction equation

HRID 571585 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.[B:33](OCC)([O:37]CC)[O:34]CC.Cl>C1COCC1.CCCCCC>[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:33]([OH:37])[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

7

Reactant 4

HCID 313Hydrochloric AcidHCID 9009Triethyl borateHCID 222471632-Bromo-9,10-diphenylanthraceneHCID 178418339Butyllithium

Product 1

HCID 231602159,10-Diphenylanthracene-2-boronic AcidYield 72%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
-80 °C

Procedure

An amount of 4.68 g (11.4 mmol) of 2-bromo-9,10-diphenylanthracene was dissolved in dehydrated THF and cooled to −80° C. An amount of 7.9 ml (12 mmol) of a solution of n butyllithium in n hexane was added dropwise and, 40 minutes later, 3.33 g (22.8 mmol) of triethyl borate was further added. After two-hour reaction, a dilute hydrochloric acid solution was added and the mixture was allowed to stand for 12 hours. Then, the separated organic layer was recrystallized to obtain 3.07 g (8.2 mmol) of 9,10-diphenylanthracene-2-boronic acid. The yield was 72%.

Workup

  1. customAfter two-hour reaction
  2. customThen, the separated organic layer was recrystallized

Sources & evidence

ORD record
ord-a947384fde994a8ba14ccba443028888
Source dataset
uspto-grants-2015_05
Patent number
US09028976B2

Reaction notes

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