Phenol → 5-Bromo-2-(1-phenoxyethyl)pyridine

HRID 1501110노트

반응식

HRID 1501110 반응식
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([OH:10])[CH3:9])=[N:6][CH:7]=1.[C:11]1(O)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH3:9])=[N:6][CH:7]=1

참가 물질

6

반응물 4

HCID 996PhenolHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 426142881-(5-Bromopyridin-2-yl)ethanol

생성물 1

HCID 895810635-Bromo-2-(1-phenoxyethyl)pyridine수율 94.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of 1-(5-bromopyridin-2-yl)ethanol (1.0 g, 4.95 mmol), phenol (835 mg, 8.87 mmol), and triphenylphosphine (1.8 g, 6.86 mmol) was stirred in dry tetrahydrofuran (70 mL) at 0° C. under nitrogen atmosphere. To this mixture was added dropwise diisopropyl diazene-1,2-dicarboxylate (1.4 g, 6.92 mmol) over 5 minutes, and the reaction was monitored by thin layer chromatography. After complete disappearance of starting material, the solvent was removed under reduced pressure and the resultant oil was purified by flash column chromatography (hexane/ethyl acetate, 1/1) to give 5-bromo-2-(1-phenoxyethyl)pyridine (1.3 g, 94.4%) as a white solid. LRMS (M+H+) m/z: calcd 278.01. found 278 1H NMR (300 MHz, DMSO) δ 8.60 (d, J=2.1 Hz, 1H), 7.93 (dd, J1=8.4 Hz, J2=2.1 Hz, 1H), 7.41 (d, J=8.4 Hz, 1H), 7.18 (m, 2H), 6.86 (m, 3H), 5.39 (m, 1H), 1.63 (d, J=6.3 Hz, 3H).

후처리

  1. customAfter complete disappearance of starting material, the solvent was removed under reduced pressure
  2. customthe resultant oil was purified by flash column chromatography (hexane/ethyl acetate, 1/1)

출처 및 근거

ORD 기록
ord-a5ed972f73114138a8c02eb6836e222c
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09206128B2

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