4-Acetyl-2-fluorobenzonitrile → 2-Fluoro-4-(2-hydroxypropan-2-yl)benzonitrile

HRID 844018

반응식

HRID 844018 반응식
[CH3:1][Mg]Cl.[C:4]([C:7]1[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[C:9]([F:15])[CH:8]=1)(=[O:6])[CH3:5]>O1CCCC1>[F:15][C:9]1[CH:8]=[C:7]([C:4]([OH:6])([CH3:1])[CH3:5])[CH:14]=[CH:13][C:10]=1[C:11]#[N:12]

참가 물질

4

반응물 2

HCID 224816534-Acetyl-2-fluorobenzonitrileHCID 178418332HCID 178418332, 화합물

생성물 1

HCID 224816262-Fluoro-4-(2-hydroxypropan-2-yl)benzonitrile수율 72.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
0 °C

실험 절차

To a stirred suspension of CeCl3 (4.7 grams, 19.0 mmole) in tetrahydrofuran (30 ml) at 0° C. was added dropwise 3.0 M methyl magnesium chloride (6.0 ml, 19.0 mmole). The mixture was stirred at 0° C. for 45 minutes and 4-Acetyl-2-fluoro-benzonitrile (2.5 grams, 15.0 mmole) in tetrahydrofuran (20 ml) was added dropwise. The mixture was stirred at 0° C. for 1 hour and quenched with 5 ml 2 N acetic acid added dropwise. The mixture was poured into 200 ml water, acidified to pH 2 with 2 N acetic acid and extracted with ethyl acetate. The combined extracts were washed with water and brine, dried over magnesium sulfate and concentrated to give an oil which was purified via flash chromatography on silica using 50% ethyl acetate/hexane as eluent to give an oil (1.95 g). MW 179.21; MS (m/e) 179 (M+).

후처리

  1. stirringThe mixture was stirred at 0° C. for 1 hour
  2. customquenched with 5 ml 2 N acetic acid
  3. additionadded dropwise
  4. additionThe mixture was poured into 200 ml water
  5. extractionextracted with ethyl acetate
  6. washThe combined extracts were washed with water and brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated
  9. customto give an oil which
  10. customwas purified via flash chromatography on silica using 50% ethyl acetate/hexane as eluent

출처 및 근거

ORD 기록
ord-2554200d4c05417e9dd78dcec289badc
출처 데이터셋
uspto-grants-2002_04
특허 번호
US06380218B1

연결된 노트

불러오는 중…