Hydrochloric Acid → 9,9,10,10-Tetrafluoro-2,7-dihexyl-9,10-dihydrophenanthrene

HRID 1419646Notes

Reaction equation

[F:1][C:2]1([F:20])[C:15]([F:17])([F:16])[C:14]2[CH:13]=[C:12](Br)[CH:11]=[CH:10][C:9]=2[C:8]2[C:3]1=[CH:4][C:5](Br)=[CH:6][CH:7]=2.[CH2:21]([Mg]Br)[CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].Cl.[Na+].[Cl-]>C1COCC1>[F:1][C:2]1([F:20])[C:15]([F:17])([F:16])[C:14]2[CH:13]=[C:12]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH:11]=[CH:10][C:9]=2[C:8]2[C:3]1=[CH:4][C:5]([CH2:14][CH2:15][CH2:2][CH2:3][CH2:4][CH3:5])=[CH:6][CH:7]=2

Participants

Conditions

Temperature: 0 °C

Procedure

4.1 g of 9,9,10,10-tetrafluoro-2,7-dibromo-9,10-dihydrophenanthrene are dissolved in 250 ml of THF and the solution is cooled to 0° C. 120 mg of 1,3-bis(diphenylphosphine)propanenickel(lI) chloride are added, and, at 0° C., 50 mmol of hexylmagnesium bromide in 100 ml of THF are added dropwise. Stirring is continued for 4 hours, and then for a further 18 hours at 50° C. The mixture is acidified with 1N HCl, the aqueous phase is saturated with NaCl and the phases are separated. The aqueous phase is subsequently subjected to extraction a number of times with tert-butyl methyl ether. The crude product is purified by chromatography on silica gel. This gives 3.45 g of 9,9,10,10-tetrafluoro-2,7-dihexyl-9,10-dihydrophenanthrene.

Workup

waitfor a further 18 hours at 50° C
customthe phases are separated
extractionThe aqueous phase is subsequently subjected to extraction a number of times with tert-butyl methyl ether
customThe crude product is purified by chromatography on silica gel

Sources & evidence

ORD record: ord-c6b292b6af3b49b09b095928928bb757
Source dataset: uspto-grants-1999_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05888422

Reaction notes

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