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

HRID 1172762
Notes
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Reaction equation

HRID 1172762 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8470Trimethyl borateHCID 222471632-Bromo-9,10-diphenylanthraceneHCID 178418339Butyllithium

Product 1

HCID 231602159,10-Diphenylanthracene-2-boronic AcidYield 80.8%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Conditions

Temperature
-78 °C

Procedure

In an argon atmosphere, 50 mL of dehydrated THF were added to 3.5 g (8.6 mmol) of 2-bromo-9,10-diphenylanthracene, and the temperature of the mixture was cooled to −78° C. Then, 6.0 mL of n-butyllithium (in hexane, 1.6 mol/L) were dropped. After the mixture had been stirred at −78° C. for 1 hour, the temperature of the mixture was increased to 0° C. The temperature of the mixture was cooled to −78° C. again, and 2.9 mL (26 mmol) of trimethoxyborane were dropped. The mixture was stirred at −78° C. for 1 hour, and was then stirred at room temperature for 2 hours. 50 mL of 10-mass % hydrochloric acid were added, and the whole was stirred for 1 hour, followed by filtration. The resultant solid was washed with toluene to obtain 2.6 g of 9,10-diphenylanthracene-2-boronic acid (80% yield).

Workup

  1. temperaturethe temperature of the mixture was increased to 0° C
  2. temperatureThe temperature of the mixture was cooled to −78° C. again
  3. stirringThe mixture was stirred at −78° C. for 1 hour
  4. stirringwas then stirred at room temperature for 2 hours
  5. stirringthe whole was stirred for 1 hour
  6. filtrationfollowed by filtration
  7. washThe resultant solid was washed with toluene

Sources & evidence

ORD record
ord-80d354884e3e4522938feec4e777af39
Source dataset
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07833632B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes