Hydrochloric Acid → (4-(9-Phenyl-9H-carbazol-3-yl)phenyl)boronic acid

HRID 1751327Notes

Reaction equation

HRID 1751327 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]3[N:12]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[C:13]4[C:18]([C:19]=3[CH:20]=2)=[CH:17][CH:16]=[CH:15][CH:14]=4)=[CH:4][CH:3]=1.CCCCCC.C([Li])CCC.[B:38]([O:43]C)(OC)[O:39]C.Cl>O1CCCC1>[C:21]1([N:12]2[C:11]3[CH:10]=[CH:9][C:8]([C:5]4[CH:4]=[CH:3][C:2]([B:38]([OH:43])[OH:39])=[CH:7][CH:6]=4)=[CH:20][C:19]=3[C:18]3[C:13]2=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 8470Trimethyl borate2×HCID 513582933-(4-Bromophenyl)-9-phenylcarbazoleHCID 178418244HCID 178418244, compound2×

Product 1

HCID 58351149(4-(9-Phenyl-9H-carbazol-3-yl)phenyl)boronic acidYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a 300-mL three-neck flask was put 8.0 g (20 mmol) of the 3-(4-bromophenyl)-9-phenyl-9H-carbazole obtained in Reaction Scheme (b-1), the atmosphere in the flask was replaced with nitrogen, 100 mL of dehydrated tetrahydrofuran (abbreviation: THF) was then added to the flask, and the temperature was lowered to −78° C. Into this mixture solution, 15 mL (24 mmol) of a 1.65 mol/L n-butyllithium hexane solution was dropped, and the mixture solution with the n-butyllithium hexane solution added was stirred for 2 hours. To this mixture, 3.4 mL (30 mmol) of trimethyl borate was added, and the mixture with the trimethyl borate added was stirred at −78° C. for 2 hours and at room temperature for 18 hours. After the reaction, 1M diluted hydrochloric acid was added to this reaction solution until the solution became acid, and the solution with the diluted hydrochloric acid added was stirred for 7 hours. This solution was subjected to ethyl acetate extraction, and the obtained organic layer was washed with a saturated saline. After the washing, magnesium sulfate was added to the organic layer to adsorb moisture. This suspension was filtered, and the obtained filtrate was concentrated, and hexane was added thereto. The mixture was irradiated with supersonic waves and then recrystallized, so that 6.4 g of a target substance was obtained as a white powder in a yield of 88%. A reaction scheme of Step 2 is shown in (b-2) given below.

Workup

  1. customIn a 300-mL three-neck flask was put
  2. additionwas then added to the flask
  3. customwas lowered to −78° C
  4. stirringwas stirred at −78° C. for 2 hours and at room temperature for 18 hours
  5. additionwas added to this reaction solution until the solution
  6. stirringwas stirred for 7 hours
  7. extractionThis solution was subjected to ethyl acetate extraction
  8. washthe obtained organic layer was washed with a saturated saline
  9. additionAfter the washing, magnesium sulfate was added to the organic layer
  10. filtrationThis suspension was filtered
  11. concentrationthe obtained filtrate was concentrated
  12. additionhexane was added
  13. customThe mixture was irradiated with supersonic waves
  14. customrecrystallized, so that 6.4 g of a target substance
  15. customwas obtained as a white powder in a yield of 88%
  16. customA reaction scheme of Step 2

Sources & evidence

ORD record
ord-5648413b516d4ad1b7f91fd831f3a551
Source dataset
uspto-grants-2015_10
Patent number
US09159942B2

Reaction notes

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