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

HRID 1404773ノート

反応式

HRID 1404773 の反応式
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([F:10])[CH:3]=1.[CH3:11][Mg]I.[Mg].CI>C(OCC)C>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]([OH:7])[CH3:11])=[C:4]([F:10])[CH:3]=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

A solution of 4-bromo-2-fluorobenzaldehyde (5 g, 24.62 mmol) in diethyl ether (10 ml) was added to an ice-cold solution of methylmagnesium iodide prepared from magnesium (1.7 g, 73.88 mmol) and methyliodide (4.58 ml, 73.88 mmol) in diethyl ether (50 ml). The mixture was warmed stirred at RT, for 12 h, and cooled to 0° C., quenched with dil. 6N 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%), 1H-NMR (δ ppm, CDCl3, 400 MHz): δ7.40 (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. temperatureThe mixture was warmed
  2. temperaturecooled to 0° C.
  3. customquenched with dil. 6N 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-5ad0f40b00f54477b23c31c99c35f55c
出典データセット
uspto-grants-2014_12
特許番号
US08912331B2

反応ノート

読み込み中…