Tetrahydrofuran → HCID 86663082, compound

HRID 879926Notes

Reaction equation

HRID 879926 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]3[C:14]([C:15]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[C:16]4[C:21]=2[CH:20]=[CH:19][CH:18]=[CH:17]4)=[CH:13][CH:12]=[CH:11][CH:10]=3)=[CH:4][CH:3]=1.O1CCCC1.C([Li])CCC.[Br:38][C:39]1[CH:40]=[C:41]([CH:45]=[CH:46][CH:47]=1)[C:42](Cl)=[O:43]>CCCCCC>[Br:38][C:39]1[CH:40]=[C:41]([CH:45]=[CH:46][CH:47]=1)[C:42]([C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:9]3[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=3)[C:15]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[C:16]3[C:21]=2[CH:20]=[CH:19][CH:18]=[CH:17]3)=[CH:6][CH:7]=1)=[O:43]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 74377Benzoyl chloride, 3-bromo-HCID 221382759-(4-Bromophenyl)-10-phenylanthraceneHCID 178418339Butyllithium

Product 1

HCID 86663082HCID 86663082, compoundYield 29.2%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

To a 200 mL three-neck flask was added 5.0 g (12 mmol) of 9-(4-bromophenyl)-10-phenylanthracene. The air in the flask was replaced with nitrogen. Then, 65 mL of tetrahydrofuran was added thereto, and the temperature of the mixture was set to −80° C. Into this solution was dripped 8.1 mL (13 mmol) of n-butyllithium (a 1.6 mol/L hexane solution) with a syringe. After that, this solution was stirred at the same temperature for 1 hour. Then, 2.8 g (13 mmol) of 3-bromobenzoyl chloride was added to this solution, and the mixture was stirred for 18 hours while its temperature was returned to room temperature. Then, an organic substance was extracted from the aqueous layer of this mixture with ethyl acetate, and the solution of the extract and the organic layer were combined and washed with a saturated aqueous sodium chloride solution. The organic layer was dried with magnesium sulfate. Then, this mixture was gravity filtered. The obtained filtrate was concentrated to give a solid. The obtained solid was purified by silica gel column chromatography (with a developing solvent of hexane and toluene in a 5:1 ratio) to give 1.8 g of a light-yellow solid in a yield of 28%. A reaction scheme of the above synthesis method is illustrated in the following (H-1).

Workup

  1. customwas set to −80° C
  2. stirringthe mixture was stirred for 18 hours while its temperature
  3. customwas returned to room temperature
  4. extractionThen, an organic substance was extracted from the aqueous layer of this mixture with ethyl acetate
  5. extractionthe solution of the extract
  6. washwashed with a saturated aqueous sodium chloride solution
  7. dry with materialThe organic layer was dried with magnesium sulfate
  8. filtrationfiltered
  9. concentrationThe obtained filtrate was concentrated
  10. customto give a solid
  11. customThe obtained solid was purified by silica gel column chromatography (with a developing solvent of hexane and toluene in a 5:1 ratio)

Sources & evidence

ORD record
ord-25655ce97997475db7e489a50dc4338a
Source dataset
uspto-grants-2015_03
Patent number
US08993127B2

Reaction notes

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