Hydrochloric Acid → HCID 57539980, compound

HRID 2405462Notes

Reaction equation

HRID 2405462 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[CH:10][C:11]3[C:12]4[C:17]([C:18]5[C:23]=3[C:22]=2[CH:21]=[CH:20][CH:19]=5)=[CH:16][CH:15]=[CH:14][CH:13]=4)[CH:5]=[CH:6][CH:7]=1.C([Li])CCC.[B:29](OC(C)C)([O:34]C(C)C)[O:30]C(C)C.Cl>CCCCCC.O1CCCC1>[CH:9]1[C:8]2=[C:22]3[C:21]([C:5]4[C:4]2=[CH:3][CH:2]=[CH:7][CH:6]=4)=[CH:20][CH:19]=[CH:18][C:23]3=[C:11]([C:12]2[CH:13]=[C:14]([B:29]([OH:34])[OH:30])[CH:15]=[CH:16][CH:17]=2)[CH:10]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 21531Triisopropyl borateHCID 59524089HCID 59524089, compoundHCID 178418339Butyllithium

Product 1

HCID 57539980HCID 57539980, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
-70 °C

Procedure

A flask was charged with 9.2 g of 3-(3-bromophenyl)fluoranthene and 129 mL of tetrahydrofuran. After cooling the reaction solution to −70° C., 17.2 mL of a 1.65 M hexane solution of n-butyllithium was added dropwise to the reaction solution. The mixture was stirred at −70° C. for 2 hours. After the dropwise addition of 17.7 mL of triisopropyl borate to the reaction solution, the reaction solution was stirred at −70° C. for 1 hour. The reaction solution was then stirred for 5 hours while heating the reaction solution to room temperature. After the addition of 2 M hydrochloric acid to the reaction solution so that the reaction solution had a pH in the acidic region, the reaction solution was extracted with ethyl acetate. After removing the aqueous phase, the organic phase was washed with a saturated sodium chloride solution, and dried over anhydrous sodium sulfate. After filtering the organic phase, the solvent was evaporated under reduced pressure. The residue was washed with a hexane-ethyl acetate mixture to obtain 7.9 g of the target 3-(fluoranthen-3-yl)phenylboronic acid (yield: 95%).

Workup

  1. stirringthe reaction solution was stirred at −70° C. for 1 hour
  2. stirringThe reaction solution was then stirred for 5 hours
  3. temperaturewhile heating the reaction solution to room temperature
  4. extractionthe reaction solution was extracted with ethyl acetate
  5. customAfter removing the aqueous phase
  6. washthe organic phase was washed with a saturated sodium chloride solution
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationAfter filtering the organic phase
  9. customthe solvent was evaporated under reduced pressure
  10. washThe residue was washed with a hexane-ethyl acetate mixture

Sources & evidence

ORD record
ord-5b7ab37fb8c04a748232503bfe7dd07e
Source dataset
uspto-grants-2014_08
Patent number
US08803420B2

Reaction notes

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