Triphenylphosphine → 3-Fluoro-2-nitro-N-(triphenylphosphoranylidene)benzenamine

HRID 1922755노트

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HRID 1922755 반응식
[N:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([F:10])[C:5]=1[N+:11]([O-:13])=[O:12])=[N+]=[N-].[C:14]1([P:20]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C1COCC1.O>[F:10][C:6]1[C:5]([N+:11]([O-:13])=[O:12])=[C:4]([N:1]=[P:20]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:9]=[CH:8][CH:7]=1

참가 물질

5

반응물 2

HCID 11776TriphenylphosphineHCID 220529091-Azido-3-fluoro-2-nitrobenzene

생성물 1

HCID 596055033-Fluoro-2-nitro-N-(triphenylphosphoranylidene)benzenamine수율 73.7%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 1-azido-3-fluoro-2-nitrobenzene (500 mg, 2.75 mmol) in THF (4 mL) and water (1 mL) was added triphenylphosphine (720 mg, 2.75 mmol). The reaction mixture was stirred at room temperature for 45 min then partitioned between water and EtOAc. The organic layer was separated and washed with brine, dried over Na2SO4, filtered and concentrated. The residue was subjected to flash chromatography (Si—PCC, Et2O) to give the desired product as a yellow solid (844 mg, 73%). LCMS (Method A): RT 4.36 min; [M+H]+ 417

후처리

  1. customthen partitioned between water and EtOAc
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-c1e1f90bd9194312b9b737cbd4fdedbe
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08173650B2

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