Hydrochloric Acid → 4-(2-Naphthyl)phenylboronic Acid

HRID 1662913Notes

Reaction equation

HRID 1662913 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([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:4][CH:3]=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:5]1[CH:6]=[CH:7][C:2]([B:29]([OH:34])[OH:30])=[CH:3][CH:4]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 8058HexaneHCID 21531Triisopropyl borateHCID 54617522-(4-Bromophenyl)naphthaleneHCID 178418339Butyllithium

Product 1

HCID 453822584-(2-Naphthyl)phenylboronic AcidYield 84%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-60 °C

Procedure

Under an argon gas atmosphere, a mixture of 50.0 g (177 mmol) of 2-(4-bromophenyl)naphthalene and 500 mL of dehydrated THF was cooled down to −60 degrees C., and added with 136 mL (212 mmol) of hexane solution of 1.56M n-butyllithium in drops while being stirred. Then, the reaction mixture was stirred for one hour at −60 degrees C. 99.6 g (529 mmol) of triisopropyl borate was dropped into the reaction solution at −60 degrees C. Subsequently, the reaction mixture was warmed up to room temperature, and stirred for 18 hours. The reaction mixture was further added with solution of hydrochloric acid to be stirred for one hour at room temperature. After the reaction, the reaction mixture was further added with 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 crystallizing the obtained solid by toluene, 33.6 g of 4-(2-naphthyl)phenylboronic acid was obtained at an yield of 84%.

Workup

  1. stirringThen, the reaction mixture was stirred for one hour at −60 degrees C
  2. temperatureSubsequently, the reaction mixture was warmed up to room temperature
  3. stirringstirred for 18 hours
  4. stirringto be stirred for one hour at room temperature
  5. customAfter the reaction
  6. dry with materialAfter organic phase thereof was dried with magnesium sulfate
  7. distillationthe solvent was distilled away under reduced pressure
  8. customBy crystallizing the obtained solid by toluene

Sources & evidence

ORD record
ord-2ad07f30b0fa4e01840d7b41dc0ab2a1
Source dataset
uspto-grants-2011_10
Patent number
US08034256B2

Reaction notes

Loading…