Trifluoroacetic acid → 3-Fluoro-2-nitroaniline

HRID 1922756ノート

反応式

HRID 1922756 の反応式
[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

参加物

4

反応物 2

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

生成物 1

HCID 27828343-Fluoro-2-nitroaniline収率 100%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-251f3171515042f59e4c3603062d5519
出典データセット
uspto-grants-2012_05
特許番号
US08173650B2

反応ノート

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