Tetrahydrofuran → HCID 23364881, compound

HRID 1080569Notes

Reaction equation

HRID 1080569 reaction equation
O1CCCC1.[Cl-].[F:7][C:8]1[CH:9]=[C:10]([Zn+])[CH:11]=[C:12]([F:15])[C:13]=1[F:14].[Cl-].[Li+].[Cl-].[NH4+].FC(F)(F)S(O[C:27]1[CH:32]=[CH:31][C:30]([CH:33]2[CH2:38][CH2:37][Si:36]([CH2:45][CH2:46][CH2:47][CH2:48][CH3:49])([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[CH2:35][CH2:34]2)=[CH:29][C:28]=1[F:50])(=O)=O>[Cl-].[Zn+2].[Cl-].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CN(C)C=O>[CH2:45]([Si:36]1([C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=2)[CH2:37][CH2:38][CH:33]([C:30]2[CH:31]=[CH:32][C:27]([C:10]3[CH:9]=[C:8]([F:7])[C:13]([F:14])=[C:12]([F:15])[CH:11]=3)=[C:28]([F:50])[CH:29]=2)[CH2:34][CH2:35]1)[CH2:46][CH2:47][CH2:48][CH3:49]

Participants

9

Reactant 5

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 433294Lithium ChlorideHCID 22369354HCID 22369354, compoundHCID 178505964HCID 178505964, compound

Product 1

HCID 23364881HCID 23364881, compoundYield 85.1%

Reagents, catalysts & solvents 3

HCID 3007855ZincchlorideCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

40 ml of a tetrahydrofuran solution of 0.8 moles of 3,4,5-trifluorophenylzinc chloride prepared by reaction between a corresponding Grignard reagent and zinc chloride was dropped in a mixture of 10.0 g of (2-fluoro-4-(4-n-pentyl-4-phenyl-4-silacyclohexyl)phenyl) trifluoromethanesulfonate, 100 mg of tetrakis(triphenylphosphine)palladium (0), 500 mg of lithium chloride and 50 ml of N,N-dimethylformamide. After agitation at 50° C. for 8 hours, the mixture was charged into an ammonium chloride aqueous solution, followed by extraction with ethyl acetate. The ethyl acetate solution was washed with brine, dried, and concentrated, followed by purification of the resultant residue through silica gel chromatography to obtain 8.20 g (yield: 75%) of 4-(4-n-pentyl-4-phenyl-4-silacyclohexyl)-2,3',4',5'-tetrafluorobiphenyl. The results of IR and 1H-NMR analyses of the product are shown below.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe ethyl acetate solution was washed with brine
  3. customdried
  4. concentrationconcentrated
  5. customfollowed by purification of the resultant residue through silica gel chromatography

Sources & evidence

ORD record
ord-90bb6ece3d68451eb28f14cdfc083a9b
Source dataset
uspto-grants-1996_12
Patent number
US05582765

Reaction notes

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