Hydrochloric Acid → (4-Phenylnaphthalen-1-yl)boronic acid

HRID 1014905Notes

Reaction equation

HRID 1014905 reaction equation
Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:4][CH:3]=1.C1([B:24]([OH:26])[OH:25])C=CC=CC=1.C1(C)C=CC=CC=1.Cl>CCOCC>[C:12]1([C:5]2[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[C:2]([B:24]([OH:26])[OH:25])=[CH:3][CH:4]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 66827Phenylboronic AcidHCID 122750251-Bromo-4-phenylnaphthalene

Product 1

HCID 45382260(4-Phenylnaphthalen-1-yl)boronic acidYield 80%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
-40 °C

Procedure

To 14 g of 1-bromo-4-phenylnaphthalene synthesized in accordance with a conventional process or by the reaction of 1-bromo-4-iodo-naphthanlene and phenylboronic acid, 130 ml of anhydrous ether and 50 ml of anhydrous toluene were added, and the reaction system was purged with argon and cooled at −40° C. To the cooled mixture, 37 ml of a 1.6 M hexane solution of normal-butyllithium was added dropwise, and the resultant mixture was stirred for 1 hour. After the obtained mixture was heated to −5° C. and then cooled to −40° C., a solution obtained by diluting 34 ml of boronic acid triisopropyl ester with ether was added dropwise, and the resultant mixture was stirred for 3.5 hours and then left standing for one night. After the resultant mixture was acidified with a 10% dilute hydrochloric acid, the reaction mixture was subjected to extraction with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride and dried with anhydrous sodium sulfate, and the solvent was removed using an evaporator. The obtained white solid substance was washed with methylene chloride and dried, and 10 g of 1-phenylnaphthalene-4-boronic acid was obtained as white crystals (the yield: 80%).

Workup

  1. additionwere added
  2. customthe reaction system was purged with argon
  3. additionTo the cooled mixture, 37 ml of a 1.6 M hexane solution of normal-butyllithium was added dropwise
  4. temperatureAfter the obtained mixture was heated to −5° C.
  5. temperaturecooled to −40° C.
  6. customa solution obtained
  7. additionwas added dropwise
  8. waitleft
  9. waitstanding for one night
  10. extractionthe reaction mixture was subjected to extraction with ethyl acetate
  11. washThe extract was washed with a saturated aqueous solution of sodium chloride
  12. dry with materialdried with anhydrous sodium sulfate
  13. customthe solvent was removed
  14. customan evaporator
  15. washThe obtained white solid substance was washed with methylene chloride
  16. customdried

Sources & evidence

ORD record
ord-dab3fddb188943aaac706dfe97613d46
Source dataset
uspto-grants-2011_07
Patent number
US07985491B2

Reaction notes

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