Styrene → HCID 21249639, compound

HRID 2268101Notes

Reaction equation

HRID 2268101 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH3:18])=[CH:12][CH:11]=2)[CH:5]=[C:4]([F:19])[C:3]=1OB(O)O.FC1C=C(C=C(F)C=1)C=O.[I-].C(OC1C=CC(C[P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1)C.C=CC1C=CC=CC=1.Br[C:73]1[CH:78]=[CH:77][C:76]([F:79])=[C:75]([F:80])[CH:74]=1.C([O-])([O-])=O.[Na+].[Na+]>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.C1(C)C=CC=CC=1>[CH2:17]([O:16][C:13]1[CH:14]=[CH:15][C:10]([CH2:9][CH2:8][C:6]2[CH:7]=[C:2]([F:1])[C:3]([C:73]3[CH:78]=[CH:77][C:76]([F:79])=[C:75]([F:80])[CH:74]=3)=[C:4]([F:19])[CH:5]=2)=[CH:11][CH:12]=1)[CH3:18]

Participants

9

Reactant 6

HCID 7501StyreneHCID 10340Sodium CarbonateHCID 676754-Bromo-1,2-difluorobenzeneHCID 5881603,5-DifluorobenzaldehydeHCID 18348272HCID 18348272, compoundHCID 18348273HCID 18348273, compound

Product 1

HCID 21249639HCID 21249639, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 9.2 g of 2,6-difluoro-4-[2-(p-ethoxyphenyl)ethyl]phenylboric acid (prepared by reacting 3,5-difluorobenzaldehyde with p-ethoxybenzyltriphenylphosphonium iodide by the Wittig method and subsequently hydrogenating the resultant styrene derivative on Pd/C), 5.9 g of 1-bromo-3,4-difluorobenzene, 38 ml of 2 molar aqueous Na2CO3 solution, 0.6 g of tetrakis(triphenylphosphine)palladium(0) and 75 ml of toluene is refluxed for two hours. The aqueous phase is extracted twice with toluene and combined with the organic phase. Customary aqueous work-up and chromatographic purification of the residue give 4-[2-(p-ethoxyphenyl)ethyl]-2,6,3′, 4′-tetrafluorobiphenyl, C 92 I, Δε+24.

Workup

  1. customprepared
  2. temperatureis refluxed for two hours
  3. extractionThe aqueous phase is extracted twice with toluene
  4. customCustomary aqueous work-up and chromatographic purification of the residue

Sources & evidence

ORD record
ord-c442d615d8f94a169cb8c012253f49dd
Source dataset
uspto-grants-2001_12
Patent number
US06326066B1

Reaction notes

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