Hydrochloric Acid → HCID 86660652, compound

HRID 1429331Notes

Reaction equation

HRID 1429331 reaction equation
Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([C:12]2C3C([C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][C:24]=4[CH:25]=2)=CC=CC=3)[CH:3]=1.C([Li])CCC.[B:31](OC(C)C)([O:36]C(C)C)[O:32]C(C)C.Cl.[CH3:45][CH2:46][CH2:47][CH2:48][CH2:49][CH3:50]>ClCCl.C1COCC1>[CH:23]1[C:24]2[CH:25]=[C:12]([C:4]3[CH:5]=[C:6]([B:31]([OH:36])[OH:32])[C:7]4[C:2](=[CH:11][CH:10]=[CH:9][CH:8]=4)[CH:3]=3)[C:46]3[C:47](=[CH:48][CH:49]=[CH:50][CH:45]=3)[C:19]=2[CH:20]=[CH:21][CH:22]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 8058HexaneHCID 21531Triisopropyl borateHCID 86660651HCID 86660651, compoundHCID 178418339Butyllithium

Product 1

HCID 86660652HCID 86660652, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-70 °C

Procedure

In argon atmosphere, a liquid mixture of 16.00 (41.74 mmol) of 4-bromo-2-(9-phenanthrenyl)naphthalene and 160 ml of dry THF was cooled to −70° C., and 32.2 ml (38.4 mmol) of a 1.56 M hexane solution of n-butyllithium was added dropwise under stirring. Further, the reaction mixture was stirred at −70° C. for 3 h. After adding 18.06 g (96.04 mmol) of triisopropyl borate while maintaining the temperature at −60° C. or lower, the mixture was stirred for one hour. The reaction mixture was heated, stirred at room temperature for 3 h, and left standing overnight. The reaction mixture was added with 50 ml of a concentrated hydrochloric acid while maintaining the temperature at 20° C. or lower by cooling on an ice bath and then stirred at room temperature for one hour. The reaction mixture was added with dichloromethane and allowed to separate into liquid phases. The organic phase was washed with water and dried over anhydrous sodium sulfate, and the solvent was removed by distillation. After recrystallizing from toluene, 5.40 g (yield: 37%) of 2-(9-phenanthrenyl)naphthalene-4-boronic acid was obtained.

Workup

  1. stirringFurther, the reaction mixture was stirred at −70° C. for 3 h
  2. temperaturewhile maintaining the temperature at −60° C.
  3. stirringlower, the mixture was stirred for one hour
  4. temperatureThe reaction mixture was heated
  5. stirringstirred at room temperature for 3 h
  6. waitleft
  7. temperaturewhile maintaining the temperature at 20° C.
  8. temperaturelower by cooling on an ice bath
  9. stirringstirred at room temperature for one hour
  10. customto separate into liquid phases
  11. washThe organic phase was washed with water
  12. dry with materialdried over anhydrous sodium sulfate
  13. customthe solvent was removed by distillation
  14. customAfter recrystallizing from toluene

Sources & evidence

ORD record
ord-53edc2831f654c8997ba4ef2f0b966f8
Source dataset
uspto-grants-2015_01
Patent number
US08940412B2

Reaction notes

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