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

HRID 248773

반응식

HRID 248773 반응식
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]

참가 물질

6

반응물 4

HCID 8028Tetrahydrofuran2회HCID 24408BromineHCID 108993711,2-Difluoro-3-trimethylsilylbenzeneHCID 197620544-Bromo-2,3-difluorobenzonitrile

생성물 1

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

시약·촉매·용매 1

HCID 178418751HCID 178418751, 화합물촉매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-4679fff0ca9d4793a7eb00ae899d2e92
출처 데이터셋
uspto-grants-1993_05
특허 번호
US05211878

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