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

HRID 909955Notes

Reaction equation

HRID 909955 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.[B:29](OC(C)C)([O:34]C(C)C)[O:30]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:29]([OH:34])[OH:30])[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
-10 °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 −10 degrees C., and added with 600 ml (948 mmol) of hexane solution of 1.6M n-butyllithium in drops while being stirred. Then, the reaction mixture was stirred for two hours at 0 degree C. The reaction solution was further cooled down to −78 degrees C., and added with 450 g (2.39 mol) of triisopropyl borate in drops. Subsequently, the reaction mixture was stirred for 17 hours at room temperature. The reaction mixture was further added with solution of hydrochloric acid to be stirred for one hour at room temperature. The reaction mixture was further added with 3 L of toluene, so that 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. stirringThen, the reaction mixture was stirred for two hours at 0 degree C
  2. temperatureThe reaction solution was further cooled down to −78 degrees C
  3. stirringSubsequently, the reaction mixture was stirred for 17 hours at room temperature
  4. stirringto be stirred for one hour at room temperature
  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-b04c94187780413798a4b3913a2f10f5
Source dataset
uspto-grants-2011_09
Patent number
US08021574B2

Reaction notes

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