Hydrochloric Acid → [3-(Naphthalen-2-yl)phenyl]boronic acid

HRID 1045293Notes

Reaction equation

HRID 1045293 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2[CH:17]=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=2)[CH:5]=[CH:6][CH:7]=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>[CH:9]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:16]=[CH:17][C:8]=1[C:4]1[CH:3]=[C:2]([B:33]([OH:34])[OH:32])[CH:7]=[CH:6][CH:5]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 8058HexaneHCID 21531Triisopropyl borateHCID 230807732-(3-Bromophenyl)naphthaleneHCID 178418339Butyllithium

Product 1

HCID 45382255[3-(Naphthalen-2-yl)phenyl]boronic acidYield 67.9%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
78 °C

Procedure

Under an argon gas atmosphere, a mixture of 212 g (748 mmol) of 2(3-bromophenyl)naphthalene and 3 L of dehydrated THF was cooled down to minus 10 degree C., and 600 ml (948 mmol) of hexane solution of 1.6M n-butyllithium was dropped into the mixture while the mixture was being stirred. Then, the mixture was stirred at 0 degree C. for 2 hours. The reaction solution was again cooled down to minus 78 degrees C., and 450 g (2.39 mol) of triisopropylborate was dropped into the solution. Then, the solution was 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. The reaction mixture was added with 3 L of toluene, and aqueous phase thereof was eliminated. After organic phase thereof was dried with magnesium sulfate, the solvent was distilled away under reduced pressure. By recrystallizing the obtained solid by toluene, 126 g of 3-(2-naphthyl)phenylboronic acid was obtained at an yield of 67%.

Workup

  1. temperaturewas cooled down to minus 10 degree C
  2. stirringThen, the mixture was stirred at 0 degree C
  3. stirringThen, the solution was stirred at room temperature for 17 hours
  4. stirringstirred at room temperature for 1 hour
  5. dry with materialAfter organic phase thereof was dried with magnesium sulfate
  6. distillationthe solvent was distilled away under reduced pressure
  7. customBy recrystallizing the obtained solid by toluene

Sources & evidence

ORD record
ord-6957a9d711534eab8cd404aff147b96f
Source dataset
uspto-grants-2013_10
Patent number
US08568903B2

Reaction notes

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