Methyl iodide → 1-(4-Bromo-2-fluorophenyl)ethanol

HRID 239633ノート

反応式

HRID 239633 の反応式
C[Mg]I.[Mg].[CH3:5]I.[Br:7][C:8]1[CH:15]=[CH:14][C:11]([CH:12]=[O:13])=[C:10]([F:16])[CH:9]=1>C(OCC)C>[Br:7][C:8]1[CH:15]=[CH:14][C:11]([CH:12]([OH:13])[CH3:5])=[C:10]([F:16])[CH:9]=1

参加物

6

反応物 4

HCID 6328Methyl iodideHCID 1435174-Bromo-2-fluorobenzaldehydeHCID 5462224MagnesiumHCID 178418373HCID 178418373、化合物

生成物 1

HCID 596944341-(4-Bromo-2-fluorophenyl)ethanol

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒2 回

実験手順

To a ice-cold solution of methyl magnesium iodide prepared from magnesium (1.7 g, 73.88 mmoles) and methyl iodide (4.58 ml, 73.88 mmoles) in diethyl ether (50 ml), 4-bromo-2-fluorobenzaldehyde(5 g, 24.62 mmoles) in diethyl ether(10 ml) was added and warmed to room temperature. After 12 h, the reaction mixture was cooled to 0° C., quenched with dilute HCl and extracted with ethyl acetate. The organic layer was dried over sodium sulphate and concentrated under reduced pressure to afford the title compound as red colour liquid (5 g, 94% yield). 1H-NMR (δ ppm, CDCl3, 400 MHz): δ 7.40(t, J=8.2 Hz, 1H), 7.30(dd, J=8.3,1.7 Hz, 1H), 7.21(dd, J=9.9,1.9 Hz, 1H), 5.17(q, J=6.4 Hz, 1H), 1.49(d, J=6.5 Hz, 3H).

後処理

  1. additionwas added
  2. temperaturethe reaction mixture was cooled to 0° C.
  3. customquenched with dilute HCl
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic layer was dried over sodium sulphate
  6. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-686d52f15c2b49d3b5ee8ba33c5d5f54
出典データセット
uspto-grants-2014_02
特許番号
US08642607B2

反応ノート

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