Hydrochloric Acid → (4-(Naphthalen-1-yl(phenyl)amino)phenyl)boronic acid

HRID 751746Notes

Reaction equation

HRID 751746 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([N:8]([C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:18]=[CH:17][CH:16]=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.C([Li])CCC.[B:30](OC(C)C)([O:35]C(C)C)[O:31]C(C)C.Cl>CCOCC.CCCCCC.C1(C)C=CC=CC=1>[C:15]1([N:8]([C:5]2[CH:4]=[CH:3][C:2]([B:30]([OH:35])[OH:31])=[CH:7][CH:6]=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17][CH:16]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 21531Triisopropyl borateHCID 18398525N-(4-Bromophenyl)-N-phenyl-1-naphthylamineHCID 178418339Butyllithium

Product 1

HCID 23088379(4-(Naphthalen-1-yl(phenyl)amino)phenyl)boronic acidYield 60.2%

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

Under an ambient atmosphere of argon gas, cooling a solution prepared by mixing 18.7 g of N-(4-bromophenyl)-N-phenyl-1-naphthylamine, 100 milliliter of dried ethyl ether and 100 milliliter of dried toluene down to a temperature of −78° C., a hexane solution of 1.6M normal butyllithium in an amount 32.8 milliliter was dripped into the cooled solution. The reacted solution was stirred for 1 hour while warming up to a temperature of 0° C. Cooling the reacted solution down to the temperature of −78° C. again, a solution prepared by dissolving 23.5 g of boric acid triisopropyl into dried ether in an amount of 50 milliliter was dripped down to the cooled solution. The resultant solution was further stirred at a room temperature for 5 hours. Adding 100 milliliter of 1 N hydrochloric acid and after stirring the resultant solution for 1 hour, a water layer was removed. After drying an organic layer with a use of magnesium sulfate, the solvent was distillated away under a reduced pressure. Refining a resultant solid by means of a silicagel column chromatography, 10.2 g of 4-(N-1-naphthyl-N-phenylamino)phenylboronic acid was obtained.

Workup

  1. temperatureUnder an ambient atmosphere of argon gas, cooling a solution
  2. customprepared
  3. temperatureCooling the reacted solution down to the temperature of −78° C. again
  4. customa solution prepared
  5. customa water layer was removed
  6. dry with materialAfter drying an organic layer with a use of magnesium sulfate

Sources & evidence

ORD record
ord-72c39f9390cc47e2af2470138848f388
Source dataset
uspto-grants-2008_07
Patent number
US07405326B2

Reaction notes

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