Hydrochloric Acid → HCID 68154510, compound

HRID 1968167Notes

Reaction equation

HRID 1968167 reaction equation
[C:1]1([C:7]2([C:26]3[CH:31]=[CH:30][C:29](Br)=[CH:28][CH:27]=3)[C:19]3[C:18](C4C=CC=CC=4)=[CH:17][CH:16]=[CH:15][C:14]=3[C:13]3[C:8]2=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CCCCCC.C([Li])CCC.[B:44](OC)([O:47]C)[O:45]C.Cl>O1CCCC1>[C:1]1([C:7]2([C:26]3[CH:31]=[CH:30][C:29]([B:44]([OH:47])[OH:45])=[CH:28][CH:27]=3)[C:19]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[C:13]3[C:8]2=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8470Trimethyl borateHCID 68153749HCID 68153749, compoundHCID 178418244HCID 178418244, compound

Product 1

HCID 68154510HCID 68154510, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

First, 4.0 g (10 mmol) of 9-phenyl-9-(4-bromophenyl)-phenyl-9H-fluorene was put in a 500 mL three-neck flask, 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, 7.6 mL (12 mmol) of a 1.59 mol/L n-butyllithium hexane solution was dropped, and the mixture was stirred for 2 hours. To this mixture, 1.4 mL (15 mmol) of trimethyl borate was added, and the mixture was stirred at −78° C. for 2 hours and at room temperature for 18 hours. After the reaction, this reaction solution was stirred while 1M diluted hydrochloric acid was added thereto until the solution became acid. This solution was subjected to ethyl acetate extraction, and an organic layer obtained was washed with a saturated saline. After the washing, magnesium sulfate was added to the organic layer to adsorb moisture. This suspension was filtered, the obtained filtrate was concentrated, and hexane was added thereto. The mixture was irradiated with ultrasonic waves and then recrystallized to obtain 3.5 g of the objective white powder in 97% yield. The reaction scheme of the synthesis method is shown in the following (A-1).

Workup

  1. additionwas then added to the flask
  2. customwas lowered to −78° C
  3. stirringthe mixture was stirred at −78° C. for 2 hours and at room temperature for 18 hours
  4. customAfter the reaction
  5. additionwas added
  6. extractionThis solution was subjected to ethyl acetate extraction
  7. customan organic layer obtained
  8. washwas 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 ultrasonic waves
  14. customrecrystallized

Sources & evidence

ORD record
ord-8afd584167fb43b4be2809e61aef9ce3
Source dataset
uspto-grants-2013_04
Patent number
US08421346B2

Reaction notes

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