Trimethyl borate → 9,10-Diphenylanthracene-2-boronic Acid

HRID 1172765Notes

Reaction equation

HRID 1172765 reaction equation
Br[C:2]1[CH:15]=[CH:14][C:13]2[C:4](=[C:5]([C:26]3[CH:35]=[CH:34][C:33]4[C:28](=CC=CC=4)[CH:27]=3)[C:6]3[C:11]([C:12]=2[C:16]2[CH:25]=[CH:24][C:23]4[C:18](=CC=CC=4)[CH:17]=2)=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH:3]=1.C([Li])CCC.C[O:42][B:43]([O:46]C)OC>C1COCC1>[C:26]1([C:5]2[C:6]3[C:11]([C:12]([C:16]4[CH:17]=[CH:18][CH:23]=[CH:24][CH:25]=4)=[C:13]4[C:4]=2[CH:3]=[C:2]([B:43]([OH:46])[OH:42])[CH:15]=[CH:14]4)=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH:35]=[CH:34][CH:33]=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 8470Trimethyl borateHCID 222471572-Bromo-9,10-di(naphthalen-2-yl)anthraceneHCID 178418339Butyllithium

Product 1

HCID 231602159,10-Diphenylanthracene-2-boronic AcidYield 62.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

In an argon atmosphere, 100 mL of dehydrated THF were added to 10 g (20 mmol) of 2-bromo-9,10-di(2-naphtyl)anthracene, and the temperature of the mixture was cooled to −78° C. Then, 14 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 6.6 mL (60 mmol) of trimethoxyborane were added. The mixture was stirred at −78° C. for 1 hour, and was then stirred at room temperature for 2 hours. 100 mL of 10-mass % hydrochloric were added, and the whole was stirred for 1 hour, followed by filtration. The resultant solid was washed with toluene to obtain 4.7 g of 9,10-diphenylanthracene-2-boronic acid (50% 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. addition100 mL of 10-mass % hydrochloric were added
  6. stirringthe whole was stirred for 1 hour
  7. filtrationfollowed by filtration
  8. washThe resultant solid was washed with toluene

Sources & evidence

ORD record
ord-95c1ccb31bb145ca9bf24ac3c37edd47
Source dataset
uspto-grants-2010_11
Patent number
US07833632B2

Reaction notes

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