Hydrochloric Acid → HCID 58261856, compound

HRID 1618945Notes

Reaction equation

HRID 1618945 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2[C:13]3[O:14][C:15]4[CH:20]=[CH:19][C:18]([C:21]5[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=5)=[CH:17][C:16]=4[C:12]=3[CH:11]=[C:10]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH:9]=2)[CH:5]=[CH:6][CH:7]=1.C([Li])CCC.[B:38]([O:43]C)([O:41]C)OC.Cl>CCCCCC.C(Cl)(Cl)Cl.O1CCCC1>[C:27]1([C:10]2[CH:9]=[C:8]([C:4]3[CH:3]=[C:2]([B:38]([OH:41])[OH:43])[CH:7]=[CH:6][CH:5]=3)[C:13]3[O:14][C:15]4[CH:20]=[CH:19][C:18]([C:21]5[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=5)=[CH:17][C:16]=4[C:12]=3[CH:11]=2)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 8470Trimethyl borateHCID 58261859HCID 58261859, compoundHCID 178418339Butyllithium

Product 1

HCID 58261856HCID 58261856, compoundYield 58%

Reagents, catalysts & solvents 3

HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent2×

Conditions

Temperature
-80 °C

Procedure

In a 50 mL three-neck flask was put 1.2 g (2.5 mmol) of 4-(3-bromophenyl)-2,8-diphenyldibenzofuran. The air in the flask was replaced with nitrogen. To this mixture was added 15 mL of tetrahydrofuran (THF), and this solution was cooled to −80° C. Then, 1.9 mL (3.0 mmol) of n-butyllithium (a 1.6 mol/L hexane solution) was dripped into this solution with a syringe. After that, this solution was stirred at the same temperature for 1 hour. Then, 0.56 L (5.0 mmol) of trimethyl borate was added to this solution, and the mixture was stirred for 18 hours while its temperature was returned to room temperature. After that, about 10 mL of diluted hydrochloric acid (1.0 mol/L) was added to this solution, followed by stirring for 1 hour. Then, the aqueous layer of this mixture was extracted with ethyl acetate, and the ethyl acetate solution and the organic layer were combined and washed with saturated brine. The organic layer was dried with magnesium sulfate. Then, this mixture was gravity filtered. The resulting filtrate was concentrated to give a solid, and a mixed solvent of chloroform and hexane was added to the solid. The mixture was irradiated with ultrasonic waves, whereby a solid was precipitated. This solid was collected by suction filtration to give 0.62 g of a light-brown powder in 58% yield, which was the substance to be produced.

Workup

  1. customIn a 50 mL three-neck flask was put
  2. stirringthe mixture was stirred for 18 hours while its temperature
  3. customwas returned to room temperature
  4. stirringby stirring for 1 hour
  5. extractionThen, the aqueous layer of this mixture was extracted with ethyl acetate
  6. washwashed with saturated brine
  7. dry with materialThe organic layer was dried with magnesium sulfate
  8. filtrationfiltered
  9. concentrationThe resulting filtrate was concentrated
  10. customto give a solid
  11. customThe mixture was irradiated with ultrasonic waves, whereby a solid
  12. customwas precipitated
  13. filtrationThis solid was collected by suction filtration

Sources & evidence

ORD record
ord-c9495812ed2d4a3aa5c3ea37d38c18be
Source dataset
uspto-grants-2014_07
Patent number
US08771840B2

Reaction notes

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