Tetrahydrofuran → 4-Propyl-2',3'-difluoro-4'-cyanobiphenyl

HRID 248773

Reaction equation

HRID 248773 reaction equation
Br[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([F:10])[C:3]=1[F:11].C[Si](C)(C)[C:14]1[CH:19]=[CH:18][CH:17]=[C:16](F)[C:15]=1F.BrBr.O1C[CH2:29][CH2:28][CH2:27]1>Cl[Ni](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:27]([C:14]1[CH:19]=[CH:18][C:17]([C:2]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([F:10])[C:3]=2[F:11])=[CH:16][CH:15]=1)[CH2:28][CH3:29]

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 24408BromineHCID 108993711,2-Difluoro-3-trimethylsilylbenzeneHCID 197620544-Bromo-2,3-difluorobenzonitrile

Product 1

HCID 145484904-Propyl-2',3'-difluoro-4'-cyanobiphenyl

Reagents, catalysts & solvents 1

HCID 178418751HCID 178418751, compoundCatalyst

Procedure

0.1 mol of chlorotriisopropyl orthotitanate in 20 ml of tetrahydrofuran is added at 5° C. to a mixture of 1-bromomagnesium-4-propylbenzene (prepared from 0.1 mol of 4-propyl-bromobenzene and 0.1 mol of magnesium) and 90 ml of tetrahydrofuran and the mixture is stirred at 5° to 20° C. for 30 minutes. A mixture of 1.3 g of bis-(triphenylphosphine)-nickel(II) chloride and 0.1 mol of 4-bromo-2,3-difluorobenzonitrile (prepared from 1-trimethylsilyl-2,3-difluorobenzene by conversion into the nitrile analogously to Example 1a) 1c) and subsequent bromination with bromine with removal by distillation of the resulting trimethylsilyl bromide) is added to this mixture. Stirring for 24 hours at room temperature and customary working up gives 4-propyl-2',3'-difluoro-4'-cyanobiphenyl.

Workup

  1. customwith removal
  2. distillationby distillation of the resulting trimethylsilyl bromide)
  3. additionis added to this mixture
  4. stirringStirring for 24 hours at room temperature

Sources & evidence

ORD record
ord-4679fff0ca9d4793a7eb00ae899d2e92
Source dataset
uspto-grants-1993_05
Patent number
US05211878

Linked notes

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