3-(Bromomethyl)-5-fluoro-1-benzothiophene → 5-Fluoro-3-isobutyl-benzo[b]thiophene

HRID 1693137ノート

反応式

HRID 1693137 の反応式
Br[CH2:2][C:3]1[C:7]2[CH:8]=[C:9]([F:12])[CH:10]=[CH:11][C:6]=2[S:5][CH:4]=1.[CH:13]([Mg]Br)([CH3:15])[CH3:14]>C1COCC1>[F:12][C:9]1[CH:10]=[CH:11][C:6]2[S:5][CH:4]=[C:3]([CH2:2][CH:13]([CH3:15])[CH3:14])[C:7]=2[CH:8]=1

参加物

4

反応物 2

HCID 136425923-(Bromomethyl)-5-fluoro-1-benzothiopheneHCID 178418365HCID 178418365、化合物

生成物 1

HCID 597599805-Fluoro-3-isobutyl-benzo[b]thiophene

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
50 °C

実験手順

To a solution of 3-bromomethyl-5-fluorobenzothiophene (2.0 g; cf. Raga, Manuel; Palacin, Celia; Castello, Josep Maria; Ortiz, Jose A.; Cuberes, Maria Rosa; Moreno-Manas, Marcial, Eur. J. Med. Chem. (1986), 21(4), 329-32) in THF (30 ml) was added over 5 minutes isopropylmagnesium bromide (1.0 M, 16.6 ml). The reaction mixture was stirred at 50° C. for 5 h, cooled, quenched with ice/water and ammonium chloride solution, and extracted with ethyl acetate. The organic phases were washed with water, dried and concentrated. The residue was chromatographed on silica gel using heptane/methylene chloride as eluent to obtain the title compound (1.35 g) as a yellowish oil. MS (EI): 208.3 (M)

後処理

  1. temperaturecooled
  2. customquenched with ice/water and ammonium chloride solution
  3. extractionextracted with ethyl acetate
  4. washThe organic phases were washed with water
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was chromatographed on silica gel

出典と根拠

ORDレコード
ord-251515dd99554df396bb60853627d78e
出典データセット
uspto-grants-2012_04
特許番号
US08158655B2

反応ノート

読み込み中…