Iodine → 2-(4-Bromo-phenyl)-4-(2-iodo-ethyl)-5-methyl-oxazole

HRID 1445758

반응식

HRID 1445758 반응식
[I:1]I.[Br:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:11][C:12]([CH3:18])=[C:13]([CH2:15][CH2:16]O)[N:14]=2)=[CH:6][CH:5]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1C=CC=CC=1>C1(C)C=CC=CC=1.O.C(OCC)(=O)C>[Br:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:11][C:12]([CH3:18])=[C:13]([CH2:15][CH2:16][I:1])[N:14]=2)=[CH:6][CH:5]=1

참가 물질

8

반응물 4

HCID 807IodineHCID 1049PyridineHCID 11776TriphenylphosphineHCID 108805302-(2-(4-Bromophenyl)-5-methyloxazol-4-YL)ethanol

생성물 1

HCID 589513942-(4-Bromo-phenyl)-4-(2-iodo-ethyl)-5-methyl-oxazole

시약·촉매·용매 3

HCID 962Water용매HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

반응 조건

온도
100 °C

실험 절차

Add iodine (1.90 g, 7.49 mmol) to a stirred mixture of 2-[2-(4-bromo-phenyl)-5-methyl-oxazol-4-yl]-ethanol (1.503 g, 5.33 mmol), triphenylphosphine (2.101 g, 8.01 mmol), and pyridine (1.4 mL, 17 mmol) in toluene (48 mL) and heat at 100° C. for 45 min. Cool to room temperature, add ethyl acetate and water, and separate the layers. Extract the aqueous layer twice with ethyl acetate, wash the organic layer with 0.1N HCl, dry over anhydrous magnesium sulfate, and concentrate under reduced pressure. Purify the residue by flash chromatography (SiO2, elute 0% to 10% EtOAc/hexanes) to-yield 1.804 g of the title compound as a colorless solid. 1H NMR (400 MHz, CDCl3) δ 7.89 (d, J=8.4 Hz, 2H), 7.60 (d, J=8.8 Hz, 2H), 3.49 (dd, J=7.2, 7.2 Hz, 2H), 3.11 (dd, J=7.2, 7.2 Hz, 2H), 2.39 (s, 3H).

후처리

  1. temperatureCool to room temperature
  2. customseparate the layers
  3. extractionExtract the aqueous layer twice with ethyl acetate
  4. washwash the organic layer with 0.1N HCl
  5. dry with materialdry over anhydrous magnesium sulfate
  6. concentrationconcentrate under reduced pressure
  7. customPurify the residue
  8. washby flash chromatography (SiO2, elute 0% to 10% EtOAc/hexanes) to-yield 1.804 g of the title compound as a colorless solid

출처 및 근거

ORD 기록
ord-ceb9f050bd8e44138dbb19c5551d1f16
출처 데이터셋
uspto-grants-2010_02
특허 번호
US07666871B2

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