Ethanol → 3-Fluoro-5-(hydroxymethyl)benzonitrile

HRID 1260890ノート

反応式

HRID 1260890 の反応式
[C:1]([C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([F:13])[CH:12]=1)[C:6](OC)=[O:7])#[N:2].C(O)C.[BH4-].[Li+]>O1CCCC1>[F:13][C:11]1[CH:12]=[C:3]([CH:4]=[C:5]([CH2:6][OH:7])[CH:10]=1)[C:1]#[N:2]

参加物

5

反応物 3

HCID 702EthanolHCID 4148881Lithium borohydrideHCID 26597287Methyl 3-cyano-5-fluorobenzoate

生成物 1

HCID 686622523-Fluoro-5-(hydroxymethyl)benzonitrile収率 62.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
55 °C

実験手順

(Step 2) To a mixed solution of methyl 3-cyano-5-fluorobenzoate (0.55 g) obtained in Step 1 in tetrahydrofuran:ethanol=10:1 (22 ml) was added lithium tetrahydroborate (0.10 g) at 0° C. After stirring at 55° C. for 1 hr, the reaction solution was quenched with ice and extracted with ethyl acetate. The extract was washed with 1N hydrochloric acid and then with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give 3-fluoro-5-(hydroxymethyl)benzonitrile (0.29 g).

後処理

  1. customthe reaction solution was quenched with ice
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with 1N hydrochloric acid
  4. dry with materialwith saturated brine, and dried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure

出典と根拠

ORDレコード
ord-8bfef8f7a0554b469c0a79b4e87b200c
出典データセット
uspto-grants-2013_06
特許番号
US08470859B2

反応ノート

読み込み中…