4-Fluorobenzoyl chloride → (4-Fluorophenyl)[2-methoxy-5-(2,6-dimethyl-4-nitrophenoxy)phenyl]methanone

HRID 432931노트

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HRID 432931 반응식
[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:6]([O:7][C:8]2[C:13]([CH3:14])=[CH:12][C:11]([N+:15]([O-:17])=[O:16])=[CH:10][C:9]=2[CH3:18])=[CH:5][CH:4]=1.[F:21][C:22]1[CH:30]=[CH:29][C:25]([C:26](Cl)=[O:27])=[CH:24][CH:23]=1>C(Cl)Cl.[Ti](Cl)(Cl)(Cl)Cl>[CH3:18][C:9]1[CH:10]=[C:11]([N+:15]([O-:17])=[O:16])[CH:12]=[C:13]([CH3:14])[C:8]=1[O:7][C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[C:20]([C:26]([C:25]2[CH:29]=[CH:30][C:22]([F:21])=[CH:23][CH:24]=2)=[O:27])[CH:19]=1

참가 물질

5

반응물 2

HCID 678794-Fluorobenzoyl chlorideHCID 100846724-(4-Methoxy-phenoxy)-3,5-dimethyl-nitrobenzene

생성물 1

HCID 10046205(4-Fluorophenyl)[2-methoxy-5-(2,6-dimethyl-4-nitrophenoxy)phenyl]methanone수율 53.1%

시약·촉매·용매 2

HCID 24193Titanium Tetrachloride촉매HCID 6344Dichloromethane용매

실험 절차

To a solution of 4-(4-methoxy-phenoxy)-3,5-dimethyl-nitrobenzene (2.7 g, 10 mmol) and p-fluorobenzoyl chloride (4.0 g, 3.0 mL, 25 mmol) in methylene chloride (10 mL) was added titanium tetrachloride (1M in methylene chloride, 50 mL, 50 mmol). The reaction mixture was stirred at room temperature for 3 d, poured into ice (100 g), and stirred 1 h. The organic layer was separated and the aqueous layer was extracted with methylene chloride (3×50 mL). The combined organic extracts were washed with 5% sodium carbonate (200 mL), brine (150 mL), dried and concentrated. The residue was triturated with ether-petroleum ether. The solid was collected by filtration to give the title compound of Step A (2.1 g) as a tan solid. MS (APCl−Calc.: 395.2, Found: 394.2 (M−1).

후처리

  1. stirringstirred 1 h
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with methylene chloride (3×50 mL)
  4. washThe combined organic extracts were washed with 5% sodium carbonate (200 mL), brine (150 mL)
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was triturated with ether-petroleum ether
  8. filtrationThe solid was collected by filtration

출처 및 근거

ORD 기록
ord-9a1ba7343789476e8f187b3516ee3dc7
출처 데이터셋
uspto-grants-2003_12
특허 번호
US06664291B2

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