Trifluoroacetic acid → 2-(Benzyloxy)-5-nitroaniline

HRID 1482687ノート

反応式

HRID 1482687 の反応式
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:10]=1[NH:18]C(=O)OC(C)(C)C)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O.CCCCCC.C(OCC)(=O)C>C(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:10]=1[NH2:18])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 6422Trifluoroacetic acidHCID 21226206Ethyl acetate hexaneHCID 86724342Tert-butyl (2-(benzyloxy)-5-nitrophenyl)carbamate

生成物 1

HCID 2646032-(Benzyloxy)-5-nitroaniline収率 98.7%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

To a solution of tert-butyl (2-(benzyloxy)-5-nitrophenyl)carbamate (1.0 g) in DCM (10 mL), cooled to 0° C., was added trifluoroacetic acid (5.0 mL). The reaction mixture was stirred at 0° C. for 15 minutes and then at room temperature for 30 minutes. The reaction was monitored by TLC using hexane:ethyl acetate (3:7) as mobile phase. After completion, the reaction mixture was quenched in water and neutralized with sodium bicarbonate. Product was extracted into DCM. The organic layer was washed with brine, dried over sodium sulfate and concentrated completely under reduce pressure at 40° C. Crude material was purified by trituration with diethyl ether to give 0.7 g of 2-(benzyloxy)-5-nitroaniline. 1H NMR: DMSO-d6 (400 MHz): 5.26 (s, 2H), 5.44 (s, 2H), 7.04 (d, 1H, J=8.8), 7.34 (m, 1H), 7.45 (m, 3H), 7.50 (s, 1H), 7.520 (d, 2H, J=2.8).

後処理

  1. waitat room temperature for 30 minutes
  2. customAfter completion, the reaction mixture was quenched in water and neutralized with sodium bicarbonate
  3. extractionProduct was extracted into DCM
  4. washThe organic layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated completely
  7. customat 40° C
  8. customCrude material was purified by trituration with diethyl ether

出典と根拠

ORDレコード
ord-fdb92e085a5a4eacb39676d7b5ef9883
出典データセット
uspto-grants-2016_08
特許番号
US09415049B2

反応ノート

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