1,2-Dimethoxyethane → 4-(4-(Trifluoromethoxy)phenyl)pyridine

HRID 1107288

반응식

HRID 1107288 반응식
[F:1][C:2]([F:14])([F:13])[O:3][C:4]1[CH:9]=[CH:8][C:7](B(O)O)=[CH:6][CH:5]=1.Cl.Br[C:17]1[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=1.C(COC)OC.C(=O)([O-])[O-].[Na+].[Na+]>O.C1(P(CCCC[Pd-](Cl)Cl)C2C=CC=CC=2)C=CC=CC=1>[F:1][C:2]([F:14])([F:13])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:17]2[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=2)=[CH:6][CH:5]=1

참가 물질

7

반응물 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 881004-Bromopyridinium chlorideHCID 27343864-(Trifluoromethoxy)phenylboronic acid

생성물 1

HCID 187870514-(4-(Trifluoromethoxy)phenyl)pyridine

시약·촉매·용매 2

HCID 178479790HCID 178479790, 화합물촉매HCID 962Water용매

실험 절차

A mixture of 4-(trifluoromethoxy)benzene boronic acid (2 g, 9.7 mmol), 4-bromopyridine hydrochloride (2.83 g, 14.5 mmol), diphenylphosphinobutylpalladium (II) dichloride (100 mg), dimethoxyethane (50 ml) and a 2M sodium carbonate solution (30 ml) were stirred at 85° C. for 2 hours. The solution was allowed to cool to ambient temperature diluted with water (100 ml), and extracted with ethyl acetate (2×100 ml). The combined organic layers were dried over sodium sulphate. Removal of the solvents in vacuo gave an oil which was chromatographed on silica in 30% ethyl acetate/hexane giving the title compound as an oil (1.86 g, 80%). 1H NMR (250 MHz, CDCl3) δ 8.72-8.70 (2H, d, J=6.2 Hz), 7.69-7.63 (2H, d, J=9.6 Hz), 7.49-7.47 (2H, d, J=6.2 Hz), and 7.36-7.32 (2H, d, J=9.6 Hz). m/z (ES+) 240 (M+1).

후처리

  1. extractionextracted with ethyl acetate (2×100 ml)
  2. dry with materialThe combined organic layers were dried over sodium sulphate
  3. customRemoval of the solvents in vacuo
  4. customgave an oil which
  5. customwas chromatographed on silica in 30% ethyl acetate/hexane giving the title compound as an oil (1.86 g, 80%)

출처 및 근거

ORD 기록
ord-cd14e6b7c3c444f3a6ac9cdadea5b074
출처 데이터셋
uspto-grants-2000_05
특허 번호
US06060469

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