Tetrahydrofuran → 2-Fluoro-9-phenylfluoren-9-ol

HRID 1004565Notes

Reaction equation

HRID 1004565 reaction equation
[F:1][C:2]1[C:3](=O)[C:4]2[C:12](=[CH:13][CH:14]=1)[C:11]1[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=1)[CH:5]=2.[C:16]1([Li])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C1C[O:26]CC1>C1CCCCC1.CCOCC>[F:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)([OH:26])[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 70093312HCID 70093312, compoundHCID 178506676HCID 178506676, compound

Product 1

HCID 212639632-Fluoro-9-phenylfluoren-9-olYield 90%

Reagents, catalysts & solvents 1

HCID 21895417Cyclohexane diethyletherSolvent

Procedure

To a stirred, ice-cooled solution of 2-fluorofluorenone (2.0 g, 10 mmol) in 15 mL of dry THF under N2 was added 10 mL of 2.4 M phenyllithium solution in cyclohexane-Et2O (7:3), keeping T<20° C. The mixture was quenched with water and the product isolated with EtOAc and purified by flash chromatography (7% EtOAc-hexanes) to give 2.52 g (90%) of 2-fluoro-9-phenylfluoren-9-ol.

Workup

  1. customT<20° C
  2. customThe mixture was quenched with water
  3. customthe product isolated with EtOAc
  4. custompurified by flash chromatography (7% EtOAc-hexanes)

Sources & evidence

ORD record
ord-ef2f68da6dd54c8681e9dd971d67e450
Source dataset
uspto-grants-2000_04
Patent number
US06051573

Reaction notes

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