Hydrochloric Acid → HCID 57539854, compound

HRID 1662914Notes

Reaction equation

HRID 1662914 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]3[CH:23]=[CH:22][C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[CH:15]=3)=[CH:10][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>O.C1(C)C=CC=CC=1.C1COCC1>[CH:15]1[C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:22]=[CH:23][C:14]=1[C:11]1[CH:10]=[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:13][CH:12]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 8058HexaneHCID 21531Triisopropyl borateHCID 3795200HCID 3795200, compoundHCID 178418339Butyllithium

Product 1

HCID 57539854HCID 57539854, compoundYield 68.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-60 °C

Procedure

Under an argon gas atmosphere, a mixture of 15.3 g (42.6 mmol) of 2-(4′-bromobiphenyl-4-yl)naphthalene 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 one hour at −60 degree C. The reaction mixture was further cooled down to −60 degrees C., and added with 24.0 g (1.06 mol) of triisopropyl borate in drops. Then, the mixture was warmed up to room temperature to be stirred for 16 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 cleansed with water and dried with magnesium sulfate, the solvent was distilled away under reduced pressure. By recrystallizing the obtained solid by hexane, 9.50 g of 4′-(naphthalene-2-yl)biphenyl-4-yl boronic acid was obtained at an yield of 67%.

Workup

  1. stirringThen, the reaction mixture was stirred for one hour at −60 degree C
  2. temperatureThe reaction mixture was further cooled down to −60 degrees C
  3. temperatureThen, the mixture was warmed up to room temperature
  4. stirringto be stirred for 16 hours
  5. stirringto be stirred for one hour at room temperature
  6. customAfter the reaction
  7. dry with materialdried with magnesium sulfate
  8. distillationthe solvent was distilled away under reduced pressure
  9. customBy recrystallizing the obtained solid by hexane

Sources & evidence

ORD record
ord-d69fe0d7df844aa5b8d83b63e3a1aac6
Source dataset
uspto-grants-2011_10
Patent number
US08034256B2

Reaction notes

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