Dibenzothiophene → HCID 66663716, compound

HRID 2273514Notes

Reaction equation

HRID 2273514 reaction equation
[CH:1]1[C:9]2[C:8]3C=CC=C[C:7]=3[S:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[Li][CH2:15][CH2:16][CH2:17][CH3:18].[C:19]1(=[O:40])[C:35]2[C:23]([C:24]3[CH:39]=[CH:38][CH:37]=[CH:36][C:25]=3C3[C:34]=2C=C2C=3C=CC=C2)=[CH:22][CH:21]=[CH:20]1>C1COCC1.C(OCC)(=O)C>[CH:15]1[C:8]2[C:9]3[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=3[S:6][C:7]=2[C:18]([C:19]2([OH:40])[C:35]3[CH:34]=[CH:20][CH:21]=[CH:22][C:23]=3[C:24]3[C:25]2=[CH:36][CH:37]=[CH:38][CH:39]=3)=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 3023DibenzothiopheneHCID 57353967HCID 57353967, compoundHCID 178418339Butyllithium

Product 1

HCID 66663716HCID 66663716, compoundYield 65.9%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Dibenzothiophene (9.21 g, 50 mmol) was dissolved in 100 ml of dry THF and solution was cooled to −50° C. n-BuLi (1.6 molar solution in hexanes, 40 ml, 64 mmol) was added dropwise. The reaction mixture was warmed to room temperature, stirred for 4 hours and cooled to −30° C. Dibenzofluorenone (9.0 g, 50 mmol) in 70 ml THF was added dropwise, reaction mixture was allowed to warm to room temperature and stirred overnight. The reaction mixture was diluted with ethyl acetate (75 ml), washed with brine 3 times, dried over MgSO4, filtered and evaporated. The solid residue was purified by column chromatography on silica (hexane/ethyl acetate 7/3) providing 12.0 g of 9-(dibenzo[b,d]thiophen-4-yl)-9H-fluoren-9-ol as white solid.

Workup

  1. additionwas added dropwise
  2. temperaturecooled to −30° C
  3. customreaction mixture
  4. temperatureto warm to room temperature
  5. stirringstirred overnight
  6. washwashed with brine 3 times
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. customevaporated
  10. customThe solid residue was purified by column chromatography on silica (hexane/ethyl acetate 7/3)

Sources & evidence

ORD record
ord-19f421c80a8c43a186710cd3456196c1
Source dataset
uspto-grants-2015_09
Patent number
US09123903B2

Reaction notes

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