Phenol → 1-Bromo-2-nitro-4-phenoxymethyl-benzene

HRID 2197983노트

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HRID 2197983 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][OH:9])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].[C:13]1(O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][O:9][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11]

참가 물질

6

반응물 4

HCID 996PhenolHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 24809228(4-Bromo-3-nitrophenyl)methanol

생성물 1

HCID 684618561-Bromo-2-nitro-4-phenoxymethyl-benzene수율 25%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

The product from Example 221a (0.5 g, 2.15 mmol) was combined with phenol (0.203 g, 2.15 mmol) and triphenylphosphine (0.735 g, 2.80 mmol) in anhydrous THF (7 mL) under nitrogen and the resulting solution cooled in an ice bath. To the cold solution was added dropwise diisopropylazodicarboxylate (0.467 mL, 2.37 mmol). Stirring at 0° C. was continued for 15 min then the cold bath was removed and the reaction mixture allowed to warm to room temperature and 90 min before quench and workup by pouring into dilute HCl and extraction with ether. The combined extracts were dried MgSO4, filtered and concentrated under vacuum giving the crude title compound that was purified by flash chromatography on silica gel eluting with EtOAc-hexanes to give the title compound (0.162 g, 25%).

후처리

  1. temperaturethe resulting solution cooled in an ice bath
  2. customthe cold bath was removed
  3. temperatureto warm to room temperature and 90 min
  4. custombefore quench
  5. additionworkup by pouring into dilute HCl and extraction with ether
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. customgiving the crude title compound that
  9. customwas purified by flash chromatography on silica gel eluting with EtOAc-hexanes

출처 및 근거

ORD 기록
ord-fd772206f36342e7b25d95fe335173d4
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08338605B2

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