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

HRID 844018

反応式

HRID 844018 の反応式
[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]

参加物

4

反応物 2

HCID 224816534-Acetyl-2-fluorobenzonitrileHCID 178418332HCID 178418332、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

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+).

後処理

  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

出典と根拠

ORDレコード
ord-2554200d4c05417e9dd78dcec289badc
出典データセット
uspto-grants-2002_04
特許番号
US06380218B1

関連ノート

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