Hydrochloric Acid → 4-(6-Phenylnaphthalene-2-yl)phenylboronic acid

HRID 1662916Notes

Reaction equation

HRID 1662916 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]=[C:13]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[CH:14]=3)[CH:9]=2)=[CH:4][CH:3]=1.CCCCCC.C([Li])CCC.[B:35](OC(C)C)([O:40]C(C)C)[O:36]C(C)C.Cl>C1(C)C=CC=CC=1.C1COCC1>[C:18]1([C:13]2[CH:14]=[C:15]3[C:10](=[CH:11][CH:12]=2)[CH:9]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([B:35]([OH:40])[OH:36])=[CH:3][CH:4]=2)[CH:17]=[CH:16]3)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 8058HexaneHCID 21531Triisopropyl borateHCID 575398112-(4-Bromophenyl)-6-phenylnaphthaleneHCID 178418339Butyllithium

Product 1

HCID 575398474-(6-Phenylnaphthalene-2-yl)phenylboronic acidYield 63%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-60 °C

Procedure

Under an argon gas atmosphere, a mixture of 15.3 g (42.6 mmol) of 2-(4-bromophenyl)-6-phenylnaphthalene and 200 mL of dehydrated THF was cooled down to −60 degrees C., and added with 32.8 mL (51.1 mmol) of hexane solution of 1.56M n-butyllithium in drops while being stirred. Then, the reaction mixture was stirred for two hours at −60 degrees C. 24.0 g (128 mol) 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 17 hours. The reaction mixture was cooled down to 0 degree C. to be further added with solution of hydrochloric acid, and then 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 recrystallizing residue by toluene and hexane, 8.7 g of 4-(6-phenylnaphthalene-2-yl) phenylboronic acid was obtained at an yield of 63%.

Workup

  1. stirringThen, the reaction mixture was stirred for two hours at −60 degrees C
  2. temperatureSubsequently, the reaction mixture was warmed up to room temperature
  3. stirringstirred for 17 hours
  4. temperatureThe reaction mixture was cooled down to 0 degree C
  5. stirringstirred for one hour at room temperature
  6. customAfter the reaction
  7. dry with materialAfter organic phase thereof was dried with magnesium sulfate
  8. distillationthe solvent was distilled away under reduced pressure
  9. customBy recrystallizing residue by toluene and hexane

Sources & evidence

ORD record
ord-f6e07d3117c74c41a6d7e7a2bf104804
Source dataset
uspto-grants-2011_10
Patent number
US08034256B2

Reaction notes

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