Trifluoroacetic acid → 3-Fluoro-2-nitroaniline

HRID 1922756노트

반응식

HRID 1922756 반응식
[F:1][C:2]1[C:3]([N+:28]([O-:30])=[O:29])=[C:4]([N:8]=P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:5]=[CH:6][CH:7]=1.C(O)(C(F)(F)F)=O>O>[F:1][C:2]1[C:3]([N+:28]([O-:30])=[O:29])=[C:4]([NH2:8])[CH:5]=[CH:6][CH:7]=1

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 596055033-Fluoro-2-nitro-N-(triphenylphosphoranylidene)benzenamine

생성물 1

HCID 27828343-Fluoro-2-nitroaniline수율 100%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A 2-5 mL microwave vial equipped with a magnetic follower was charged with 3-fluoro-2-nitro-N-(triphenylphosphoranylidene)benzenamine (585 mg, 1.4 mmol), water (3 mL) and TFA (0.1 mL). The reaction mixture was irradiated at 160° C. for 15 min and then partitioned between water and EtOAc. The organic layer was separated and washed with an saturated aqueous solution of sodium bicarbonate and brine, dried over Na2SO4, filtered and concentrated. The residue was subjected to flash chromatography (Si—PCC, 0-100% Et2O in pentane) to give 3-Fluoro-2-nitrophenylamine as an orange solid (218 mg, 100%). 1H NMR (CDCl3, 400 MHz): δ 7.22 (ddd, J=8.2, 8.2, 5.5 Hz, 1 H); 6.57 (ddd, J=8.5, 1.4, 1.4 Hz, 1 H); 6.48 (ddd, J=11.3, 8.2, 1.4 Hz, 1 H.

후처리

  1. customA 2-5 mL microwave vial equipped with a magnetic follower
  2. customThe reaction mixture was irradiated at 160° C. for 15 min
  3. custompartitioned between water and EtOAc
  4. customThe organic layer was separated
  5. washwashed with an saturated aqueous solution of sodium bicarbonate and brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-251f3171515042f59e4c3603062d5519
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08173650B2

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