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

HRID 584032

反応式

HRID 584032 の反応式
[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 24193Titanium Tetrachloride触媒HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-d0f5d9a26ccc446f8fe88fb81838eacd
出典データセット
uspto-grants-2005_08
特許番号
US06924310B2

関連ノート

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