1-(4-((3,4-Dichlorobenzyl)oxy)phenyl)ethanone → 2-Bromo-1-[4-(3,4-dichloro-benzyloxy)-phenyl]-ethanone

HRID 879662ノート

反応式

HRID 879662 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][C:18]=1[Cl:19])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13](=[O:15])[CH3:14])=[CH:9][CH:8]=1.C1CNC(=O)C1.[Br:26][Br-]Br>CO.C(Cl)Cl>[Br:26][CH2:14][C:13]([C:10]1[CH:9]=[CH:8][C:7]([O:6][CH2:5][C:4]2[CH:16]=[CH:17][C:18]([Cl:19])=[C:2]([Cl:1])[CH:3]=2)=[CH:12][CH:11]=1)=[O:15]

参加物

3

反応物 1

HCID 27750311-(4-((3,4-Dichlorobenzyl)oxy)phenyl)ethanone

生成物 1

HCID 583275742-Bromo-1-[4-(3,4-dichloro-benzyloxy)-phenyl]-ethanone

試薬・触媒・溶媒 1

HCID 21226129Dichloromethane methanol溶媒

実験手順

1-[4-(3,4-Dichloro-benzyloxy)-phenyl]-ethanone (2.92 g) was dissolved in methanol:DCM (2:1, 75 mL) and pyrrolidinone hydrotribromide (7.5 g) was added and stirred at room temperature for 2.5 h. After completion of the reaction, the mixture was concentrated in vacuo and poured into saturated sodium bicarbonate solution (100 mL) and extracted with ethyl acetate (2×100 mL). The organic extracts were combined and concentrated in vacuo. Then this residue was dissolved in DCM (10 ml) and methanol (10 mL) was slowly added to this solution to precipitate the product. The colored solution was filtered through to give clear white powder product 2-bromo-1-[4-(3,4-dichloro-benzyloxy)-phenyl]-ethanone with quantitative yield (3.75 g). 1H NMR (400 MHz, CDCl3): 7.98 (d, 2H), 7.54 (s, 1H), 7.47 (d, 1H), 7.25 (m, 1H), 7.01 (d, 2H), 5.09 (s, 2H), and 4.40 (s, 2H).

後処理

  1. customAfter completion of the reaction
  2. concentrationthe mixture was concentrated in vacuo
  3. additionpoured into saturated sodium bicarbonate solution (100 mL)
  4. extractionextracted with ethyl acetate (2×100 mL)
  5. concentrationconcentrated in vacuo
  6. dissolutionThen this residue was dissolved in DCM (10 ml)
  7. additionmethanol (10 mL) was slowly added to this solution
  8. customto precipitate the product
  9. filtrationThe colored solution was filtered through

出典と根拠

ORDレコード
ord-5f009e6fa03f483cbdfac8f3f19f7bc2
出典データセット
uspto-grants-2015_03
特許番号
US08987295B2

反応ノート

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