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

HRID 1045295Notes

Reaction equation

HRID 1045295 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.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:5]1[CH:6]=[CH:7][C:2]([B:33]([OH:34])[OH:32])=[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

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 minus 60 degree C. Then, 136 ml (212 mmol) of hexane solution of 1.56M n-butyllithium was dropped into the mixture while the mixture was being stirred. The reaction mixture was further stirred at minus 60 degrees for 1 hour. 99.6 g (529 mmol) of triisopropylborate was dropped into the reaction mixture at minus 60 degrees C. Subsequently, the reaction mixture was warmed up to room temperature, and stirred for 18 hours. The reaction mixture was added with aqueous solution of hydrochloric acid and stirred at room temperature for 1 hour. After the reaction, the reaction mixture was added with toluene, and aqueous phase thereof was eliminated. Then, organic phase thereof was dried with magnesium sulfate, and the solvent was distilled away under reduced pressure. By recrystallizing the obtained solid by toluene, 33.6 g of 4-(2-naphthyl)phenylboronic acid was obtained at an yield of 84%.

Workup

  1. temperaturewas cooled down to minus 60 degree C
  2. stirringThe reaction mixture was further stirred at minus 60 degrees for 1 hour
  3. stirringstirred for 18 hours
  4. stirringstirred at room temperature for 1 hour
  5. customAfter the reaction
  6. dry with materialThen, organic phase thereof was dried with magnesium sulfate
  7. distillationthe solvent was distilled away under reduced pressure
  8. customBy recrystallizing the obtained solid by toluene

Sources & evidence

ORD record
ord-f71c4560e16645bc8e0eb9d41471bfa9
Source dataset
uspto-grants-2013_10
Patent number
US08568903B2

Reaction notes

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