Hydrochloric Acid → [10-(4-tert-Butylphenyl)anthracen-9-yl]boronic acid

HRID 659920Notes

Reaction equation

HRID 659920 reaction equation
Br[C:2]1[C:3]2[C:8]([C:9]([C:16]3[CH:21]=[CH:20][C:19]([C:22]([CH3:25])([CH3:24])[CH3:23])=[CH:18][CH:17]=3)=[C:10]3[C:15]=1[CH:14]=[CH:13][CH:12]=[CH:11]3)=[CH:7][CH:6]=[CH:5][CH:4]=2.CCCCCC.[B:32](OC(C)C)([O:37]C(C)C)[O:33]C(C)C.Cl>O1CCCC1>[C:22]([C:19]1[CH:18]=[CH:17][C:16]([C:9]2[C:10]3[C:15]([C:2]([B:32]([OH:37])[OH:33])=[C:3]4[C:8]=2[CH:7]=[CH:6][CH:5]=[CH:4]4)=[CH:14][CH:13]=[CH:12][CH:11]=3)=[CH:21][CH:20]=1)([CH3:24])([CH3:25])[CH3:23]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8058HexaneHCID 21531Triisopropyl borateHCID 21076374HCID 21076374, compound

Product 1

HCID 58085473[10-(4-tert-Butylphenyl)anthracen-9-yl]boronic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

15.4 g of the above-mentioned 9-bromo-10-(4-tert-butylphenyl) anthracene was dissolved in 380 ml of tetrahydrofuran to drop 30 ml of n-butylithium (1.6 M-hexane solution) thereto under nitrogen atmosphere at a temperature of 0° C. The solution was stirred at a temperature of 0° C. for 30 minutes and thereafter cooled to a temperature of −80° C. to drop 18.2 ml of triisopropyl borate thereto. The solution was heated up to room temperature by standing at room temperature and thereafter stirred at room temperature for 3 hours. 400 ml of 10%-hydrochloric acid was dropped thereto and further stirred at room temperature for 2 hours to thereafter extract 300 ml of diethyl ether therefrom. The organic layer was washed in 100 ml of 5%-sodium carbonate aqueous solution, washed in 100 ml of water, then dried by magnesium sulfate and thereafter concentrated by evaporation. The organic layer was purified by silica gel column chromatography (developing solvent was in the order of dichloromethane/hexane=1/1, dichloromethane and dichloromethane/methanol=50/1) and vacuum dried to thereafter obtain 6.78 g of 9-(4-tert-butylphenyl)-10-anthraceneboronic acid.

Workup

  1. customat a temperature of 0° C
  2. temperaturecooled to a temperature of −80° C.
  3. temperatureThe solution was heated up to room temperature
  4. customby standing at room temperature
  5. stirringstirred at room temperature for 3 hours
  6. stirringfurther stirred at room temperature for 2 hours
  7. extractionto thereafter extract 300 ml of diethyl ether
  8. washThe organic layer was washed in 100 ml of 5%-sodium carbonate aqueous solution
  9. washwashed in 100 ml of water
  10. dry with materialdried by magnesium sulfate
  11. concentrationconcentrated by evaporation
  12. customThe organic layer was purified by silica gel column chromatography (
  13. customdried

Sources & evidence

ORD record
ord-2533c9ca0c304c8d8d861ff8da3c32af
Source dataset
uspto-grants-2011_12
Patent number
US08084146B2

Reaction notes

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