Isopropanol → 1-Chloro-4-fluoro-5-nitro-2-(propan-2-yloxy)benzene

HRID 2064187노트

반응식

HRID 2064187 반응식
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5]([F:11])=[CH:4][C:3]=1[OH:12].[CH3:13][CH:14](O)[CH3:15].C1(P(C2C=CC=CC=2)C2C=CC=CN=2)C=CC=CC=1.N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O.Cl.C(OCC)C>O1CCCC1>[Cl:1][C:2]1[C:3]([O:12][CH:14]([CH3:15])[CH3:13])=[CH:4][C:5]([F:11])=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1

참가 물질

7

반응물 5

HCID 3776IsopropanolHCID 97268Di-tert-butyl azodicarboxylateHCID 6218932-PyridyldiphenylphosphineHCID 10953452Ether hydrochlorideHCID 596853292-Chloro-5-fluoro-4-nitrophenol

생성물 1

HCID 593939321-Chloro-4-fluoro-5-nitro-2-(propan-2-yloxy)benzene수율 43.7%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A mixture of 2-chloro-5-fluoro-4-nitrophenol (287 mg, 1.5 mmol), propan-2-ol (90 mg, 1.5 mmol), diphenyl-2-pyridylphosphine (592 mg, 2.25 mmol) and di-tert-butyl azodicarboxylate (518 mg, 2.25 mmol) in tetrahydrofuran (10 ml) was stirred at room temperature under argon for 22 hrs. The mixture was treated with 1M HCl/diethyl ether (10 ml) and stirred at room temperature for 1 hr, then concentrated under vacuum and the residue dissolved in diethyl ether (10 ml), treated with 5M HCl acid (10 ml) and stirred for 30 mins. The organic layer was separated, washed with 5M HCl acid (10 ml), then 10% Na2CO3 solution (2×10 ml), dried (MgSO4) and concentrated under vacuum. The residue was purified by chromatography on silica gel eluting with 5-70% ethyl acetate/60-80 petrol ether to afford the title compound as a yellow solid (153 mg, 43%).

후처리

  1. stirringstirred at room temperature for 1 hr
  2. concentrationconcentrated under vacuum
  3. dissolutionthe residue dissolved in diethyl ether (10 ml)
  4. additiontreated with 5M HCl acid (10 ml)
  5. stirringstirred for 30 mins
  6. customThe organic layer was separated
  7. washwashed with 5M HCl acid (10 ml)
  8. dry with material10% Na2CO3 solution (2×10 ml), dried (MgSO4)
  9. concentrationconcentrated under vacuum
  10. customThe residue was purified by chromatography on silica gel eluting with 5-70% ethyl acetate/60-80 petrol ether

출처 및 근거

ORD 기록
ord-e6a2c28da9a842fd920d3797328f7bb0
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08288412B2

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