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Dimethylformamide → 4-(Benzyloxy)-1-bromo-2-fluorobenzene

HRID 707497
ノート
印刷プレビュー

反応式

HRID 707497 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[F:9].CN(C=O)C.C(=O)([O-])[O-].[K+].[K+].[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>O>[CH2:21]([O:8][C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[C:3]([F:9])[CH:4]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 27791534-Bromo-3-fluorophenol

生成物 1

HCID 222739334-(Benzyloxy)-1-bromo-2-fluorobenzene収率 102.9%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

To a mixed solution of a commercially available product of 4-bromo-3-fluorophenol (15.0 g, 78.5 mmol) and DMF (30 mL) were added potassium carbonate (21.7 g, 157 mmol) and benzyl bromide (10.2 mL, 86.4 mmol) at room temperature, and the resultant mixture was stirred at room temperature for 20 minutes and then at 70° C. for 40 minutes. The reaction mixture was cooled to room temperature, then water was added to the reaction mixture, and the resultant solution was extracted with ethyl acetate. An organic layer was washed with water and then with saturated brine. An organic layer was dried over anhydrous magnesium sulfate and then filtrated. The solvent was evaporated under a reduced pressure, and the resultant residue was purified by silica gel column chromatography (heptane:ethyl acetate=5:1) to give the title compound (22.7 g, yield: quantitative).

後処理

  1. extractionthe resultant solution was extracted with ethyl acetate
  2. washAn organic layer was washed with water
  3. dry with materialAn organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltrated
  5. customThe solvent was evaporated under a reduced pressure
  6. customthe resultant residue was purified by silica gel column chromatography (heptane:ethyl acetate=5:1)

出典と根拠

ORDレコード
ord-d385ff52753b4369a063c5f9e2ad8868
出典データセット
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09174998B2

反応ノート

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