Hydrochloric Acid → HCID 67609065, compound

HRID 2274135Notes

Reaction equation

HRID 2274135 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]3C4C([C:18]5[C:23]=3[C:22]=2[CH:21]=[CH:20][CH:19]=5)=CC=CC=4)=[CH:4][CH:3]=1.C([Li])CCC.[B:29](OC(C)C)([O:34]C(C)C)[O:30]C(C)C.Cl.[CH3:43][CH2:44][CH2:45][CH2:46][CH2:47][CH3:48]>O1CCCC1>[CH:20]1[C:21]2=[C:22]3[C:8]([C:5]4[C:6]2=[CH:7][CH:2]=[CH:3][CH:4]=4)=[CH:9][CH:10]=[CH:11][C:23]3=[C:18]([C:45]2[CH:44]=[CH:43][C:48]([B:29]([OH:34])[OH:30])=[CH:47][CH:46]=2)[CH:19]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 8058HexaneHCID 21531Triisopropyl borateHCID 23080768HCID 23080768, compoundHCID 178418339Butyllithium

Product 1

HCID 67609065HCID 67609065, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-70 °C

Procedure

In the atmosphere of argon, 9.2 g of 3-(4-bromophenyl)fluoranthene and 129 mL of tetrahydrofuran were placed in a flask. The reaction solution was cooled to −70° C., and 17.2 mL of a 1.65M hexane solution of n-butyllithium was added dropwise. Stirring was conducted at −70° C. for 2 hours. To the reaction solution, 17.7 mL of triisopropyl borate was added dropwise, and the resultant was stirred at −70° C. for 1 hour. While heating the reaction solution to room temperature, stirring was conducted for 5 hours. 2M hydrochloric acid was added to the reaction liquid to allow it to be acidic, and the reaction solution was extracted with ethyl acetate. After removing an aqueous phase, an organic phase was washed with saturated saline, and dried with anhydrous sodium sulfate. After filtration, the solvent was distilled off under reduced pressure, residues were washed with a hexane-ethyl acetate mixed solution, whereby 7.9 g (yield 95%) of 4-(fluoranthen-3-yl)phenylboronic acid was obtained.

Workup

  1. stirringthe resultant was stirred at −70° C. for 1 hour
  2. temperatureWhile heating the reaction solution to room temperature
  3. stirringstirring
  4. waitwas conducted for 5 hours
  5. extractionthe reaction solution was extracted with ethyl acetate
  6. customAfter removing an aqueous phase
  7. washan organic phase was washed with saturated saline
  8. dry with materialdried with anhydrous sodium sulfate
  9. filtrationAfter filtration
  10. distillationthe solvent was distilled off under reduced pressure, residues
  11. washwere washed with a hexane-ethyl acetate mixed solution

Sources & evidence

ORD record
ord-32d40db93c53470a9d25a95d3d6056d5
Source dataset
uspto-grants-2015_09
Patent number
US09126943B2

Reaction notes

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