Hydrochloric Acid → {10-[4-(Naphthalen-2-yl)phenyl]anthracen-9-yl}boronic acid

HRID 1045284Notes

Reaction equation

HRID 1045284 reaction equation
Br[C:2]1[C:3]2[C:8]([C:9]([C:16]3[CH:21]=[CH:20][C:19]([C:22]4[CH:31]=[CH:30][C:29]5[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=5)[CH:23]=4)=[CH:18][CH:17]=3)=[C:10]3[C:15]=1[CH:14]=[CH:13][CH:12]=[CH:11]3)=[CH:7][CH:6]=[CH:5][CH:4]=2.CCCCCC.C([Li])CCC.[B:43]([O:48]C)(OC)[O:44]C.Cl>C1(C)C=CC=CC=1.CCOCC>[CH:23]1[C:24]2[C:29](=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:30]=[CH:31][C:22]=1[C:19]1[CH:20]=[CH:21][C:16]([C:9]2[C:8]3[C:3](=[CH:4][CH:5]=[CH:6][CH:7]=3)[C:2]([B:43]([OH:48])[OH:44])=[C:15]3[C:10]=2[CH:11]=[CH:12][CH:13]=[CH:14]3)=[CH:17][CH:18]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8470Trimethyl borateHCID 23148608HCID 23148608, compoundHCID 178418244HCID 178418244, compound

Product 1

HCID 23148615{10-[4-(Naphthalen-2-yl)phenyl]anthracen-9-yl}boronic acidYield 67%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
-40 °C

Procedure

9-Bromo-10-(4-naphthalene-2-yl-phenyl)anthracene 13.8 g was dispersed in dehydrated toluene 80 ml and dehydrated ether 80 ml, and the mixture was cooled down to −30° C. A 1.58M n-butyllithium hexane solution 21. 0 ml was dropwise added thereto, and after the solution was stirred at −40° C. for 30 minutes, the temperature was elevated up to −10° C. The solution was cooled again down to −70° C., and a dehydrated ether solution of trimethyl borate 10.0 ml was gradually added thereto. The solution was stirred at −70° C. for 2 hours and then gradually heated up to room temperature. After left standing for a night, a 10% hydrochloric acid aqueous solution 100 ml was added thereto and stirred, and then it was extracted twice with toluene. The organic layer was washed with saturated brine and dried on anhydrous sodium sulfate. The solvent was distilled off, and the residue was crystallized from toluene/hexane, filtered and dried, whereby targeted 10-(4-naphthalene-2-yl-phenyl)anthracene-9-boronic acid 8.48 g was obtained in the form of yellow crystal (yield: 67%).

Workup

  1. addition0 ml was dropwise added
  2. customwas elevated up to −10° C
  3. temperatureThe solution was cooled again down to −70° C.
  4. stirringThe solution was stirred at −70° C. for 2 hours
  5. temperaturegradually heated up to room temperature
  6. waitAfter left standing for a night
  7. stirringstirred
  8. extractionit was extracted twice with toluene
  9. washThe organic layer was washed with saturated brine
  10. dry with materialdried on anhydrous sodium sulfate
  11. distillationThe solvent was distilled off
  12. customthe residue was crystallized from toluene/hexane
  13. filtrationfiltered
  14. customdried

Sources & evidence

ORD record
ord-b715d98af1014f23b9696e467e808830
Source dataset
uspto-grants-2013_10
Patent number
US08568902B2

Reaction notes

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