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

HRID 1693137노트

반응식

HRID 1693137 반응식
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

참가 물질

4

반응물 2

HCID 136425923-(Bromomethyl)-5-fluoro-1-benzothiopheneHCID 178418365HCID 178418365, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
50 °C

실험 절차

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)

후처리

  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

출처 및 근거

ORD 기록
ord-251515dd99554df396bb60853627d78e
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08158655B2

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