Hydrochloric Acid → 4-(1-Naphthyl)phenylboronic Acid (contains varying amounts of Anhydride)

HRID 1045299Notes

Reaction equation

HRID 1045299 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH:11]=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.CCCCCC.C([Li])CCC.C([O:32][B:33](OC(C)C)[O:34]C(C)C)(C)C.Cl>C1(C)C=CC=CC=1.C1COCC1>[C:8]1([C:5]2[CH:6]=[CH:7][C:2]([B:33]([OH:34])[OH:32])=[CH:3][CH:4]=2)[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10][CH:9]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 8058HexaneHCID 21531Triisopropyl borateHCID 112083381-(4-bromophenyl)naphthaleneHCID 178418339Butyllithium

Product 1

HCID 441193994-(1-Naphthyl)phenylboronic Acid (contains varying amounts of Anhydride)Yield 68.9%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Under an argon gas atmosphere, a mixture of 208.8 g (737.4 mmol) of 1-(4-bromophenyl)naphthalene and 2.1 L of dehydrated THF was cooled down to minus 60 degree C. Then, 567 ml (884.9 mmol) of hexane solution of 1.56M n-butyllithium was dropped into the mixture while the mixture was being stirred. The reaction mixture was further stirred at minus 60 degrees for 2 hours. 416 g (2.21 mol) of triisopropylborate was dropped into the reaction mixture at minus 60 degrees C. The reaction mixture was then stirred at room temperature for 17 hours. The reaction mixture was added with aqueous solution of hydrochloric acid and stirred at room temperature for 1 hour. After the reaction, the reaction mixture was added with toluene, and aqueous phase thereof was eliminated. Then, organic phase thereof was dried with magnesium sulfate, and the solvent was distilled away under reduced pressure. By recrystallizing the obtained solid by toluene, 126 g of 4-(1-naphthyl)phenylboronic acid was obtained at an yield of 67%.

Workup

  1. temperaturewas cooled down to minus 60 degree C
  2. stirringThe reaction mixture was further stirred at minus 60 degrees for 2 hours
  3. stirringThe reaction mixture was then stirred at room temperature for 17 hours
  4. stirringstirred at room temperature for 1 hour
  5. customAfter the reaction
  6. dry with materialThen, organic phase thereof was dried with magnesium sulfate
  7. distillationthe solvent was distilled away under reduced pressure
  8. customBy recrystallizing the obtained solid by toluene

Sources & evidence

ORD record
ord-7ba21a6bd01f4f52814d5dca8b509f0c
Source dataset
uspto-grants-2013_10
Patent number
US08568903B2

Reaction notes

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