Hydrochloric Acid → HCID 58544616, compound

HRID 1429336Notes

Reaction equation

HRID 1429336 reaction equation
BrC1C=CC2[O:6][C:7]3[CH:12]=[CH:11][C:10]([C:13]4[CH:22]=[CH:21][C:20]5[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=5)[CH:14]=4)=[CH:9][C:8]=3C=2C=1.C([Li])CCC.[B:30](OC(C)C)([O:35]C(C)C)[O:31]C(C)C.Cl.[CH3:44][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49]>ClCCl.C1COCC1>[CH:14]1[C:15]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:21]=[CH:22][C:13]=1[C:10]1[CH:11]=[CH:12][C:7]2[O:6][C:47]3[CH:48]=[CH:49][C:44]([B:30]([OH:35])[OH:31])=[CH:45][C:46]=3[C:8]=2[CH:9]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 8058HexaneHCID 21531Triisopropyl borateHCID 58569420HCID 58569420, compoundHCID 178418339Butyllithium

Product 1

HCID 58544616HCID 58544616, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-60 °C

Procedure

In argon atmosphere, a liquid mixture of 7.47 g (20.0 mmol) of 2-bromo-8-(naphthalene-2-yl)dibenzofuran and 75 ml of dry THF was cooled to −60° C. and 15.5 ml (24.0 mmol) of a 1.55 M hexane solution of n-butyllithium was added dropwise under stirring. Further, the reaction mixture was stirred at −70° C. for 2 h. The reaction solution was cooled again to −70° C., and 11.29 g (60.0 mol) of triisopropyl borate was added dropwise. The reaction mixture was heated up to room temperature, stirred for one hour, and left standing overnight. The reaction mixture was cooled on an ice bath, added with a 6 N hydrochloric acid, and stirred at room temperature for one hour. After adding dichloromethane, the reaction mixture was allowed to separate into liquid phases, and the organic phase was washed with water and dried over sodium sulfate. The solvent was removed by distillation under reduced pressure, and the residue was purified by silica gel chromatography to obtain 3.65 g (yield: 54%) of 8-(naphthalene-2-yl)dibenzofuran-2-ylboronic acid.

Workup

  1. stirringFurther, the reaction mixture was stirred at −70° C. for 2 h
  2. temperatureThe reaction solution was cooled again to −70° C.
  3. temperatureThe reaction mixture was heated up to room temperature
  4. stirringstirred for one hour
  5. waitleft
  6. temperatureThe reaction mixture was cooled on an ice bath
  7. stirringstirred at room temperature for one hour
  8. customto separate into liquid phases
  9. washthe organic phase was washed with water
  10. dry with materialdried over sodium sulfate
  11. customThe solvent was removed by distillation under reduced pressure
  12. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-10d230a1e57c40a08b66f4237e65df4c
Source dataset
uspto-grants-2015_01
Patent number
US08940412B2

Reaction notes

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