3-(Trifluoromethyl)benzoyl chloride → 8-nitro-2-(3-(trifluoromethyl)phenyl)-4H-chromen-4-one

HRID 876520ノート

反応式

HRID 876520 の反応式
[OH:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[C:11](=[O:13])[CH3:12].[F:14][C:15]([F:26])([F:25])[C:16]1[CH:17]=[C:18]([CH:22]=[CH:23][CH:24]=1)[C:19](Cl)=O.C1CCN2C(=NCCC2)CC1>N1C=CC=CC=1>[N+:8]([C:7]1[CH:6]=[CH:5][CH:4]=[C:3]2[C:2]=1[O:1][C:19]([C:18]1[CH:22]=[CH:23][CH:24]=[C:16]([C:15]([F:14])([F:25])[F:26])[CH:17]=1)=[CH:12][C:11]2=[O:13])([O-:10])=[O:9]

参加物

5

反応物 3

HCID 752573-(Trifluoromethyl)benzoyl chlorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 2700261-(2-Hydroxy-3-nitrophenyl)-ethanone

生成物 1

HCID 584772368-nitro-2-(3-(trifluoromethyl)phenyl)-4H-chromen-4-one収率 13.5%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

反応条件

温度
80 °C

実験手順

1-(2-Hydroxy-3-nitrophenyl)ethanone 1 (1.2 g, 6.61 mmol) was taken up in 20 mL of pyridine along with 3-trifluoromethylbenzoyl chloride 48 (1.2 mL, 7.9 mmol) and DBU (2.9 mL, 14.5 mmol). The reaction mixture was stirred at 80° C. for 18 h. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The resulting residue was diluted with EtOAc and washed with dilute 1 N HCl. The organic layer was dried (Na2SO4) and concentrated under reduced pressure. Purification by chromatography (1:1 pentane/EtOAc) afforded 300 mg of 2. MS (ESI) calcd for C16H8F3NO4: 335.04. found: 336 [M+H].

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. concentrationconcentrated under reduced pressure
  3. additionThe resulting residue was diluted with EtOAc
  4. washwashed
  5. additionwith dilute 1 N HCl
  6. dry with materialThe organic layer was dried (Na2SO4)
  7. concentrationconcentrated under reduced pressure
  8. customPurification by chromatography (1:1 pentane/EtOAc)

出典と根拠

ORDレコード
ord-928015df78a5405ab542fbf84c48df05
出典データセット
uspto-grants-2015_03
特許番号
US08987258B2

反応ノート

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