N-Fluorobenzenesulfonimide → 3-Fluoro-5-phenyl-benzo[b]thiophene-2-carboxylic acid

HRID 401684ノート

反応式

HRID 401684 の反応式
[C:1]1([C:7]2[CH:18]=[CH:17][C:10]3[S:11][C:12]([C:14]([OH:16])=[O:15])=[CH:13][C:9]=3[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Li]CCCC.C1C=CC(S(N(S(C2C=CC=CC=2)(=O)=O)[F:34])(=O)=O)=CC=1>C1COCC1>[F:34][C:13]1[C:9]2[CH:8]=[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH:18]=[CH:17][C:10]=2[S:11][C:12]=1[C:14]([OH:16])=[O:15]

参加物

5

反応物 3

HCID 588007N-FluorobenzenesulfonimideHCID 596260715-Phenylbenzo[b]thiophene-2-carboxylic acidHCID 178418339Butyllithium

生成物 1

HCID 596258253-Fluoro-5-phenyl-benzo[b]thiophene-2-carboxylic acid収率 72.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-70 °C

実験手順

To a solution of compound 52c (507 mg, 1.99 mmol) in THF (8 mL) at −70° C. was added n-BuLi (1.6 M in hexane, 2.62 mL, 4.19 mmol). The mixture was stirred at −70° C. for 1 h; then a solution of N-fluorobenzenesulfonimide (817.3 mg, 2.59 mmol) in THF (2 mL) was slowly added. The reaction mixture was allowed to warm to room temperature and was stirred overnight. The resulting mixture was partitioned between dilute aqueous HCl and EtOAc. The organic solution was washed with water and brine, dried over Na2SO4, and concentrated. The residue was tritrated from CH2Cl2, filtered and dried the solid to give compound 52d (391.9 mg). MS m/z (M+H+) 273.0.

後処理

  1. temperatureto warm to room temperature
  2. stirringwas stirred overnight
  3. customThe resulting mixture was partitioned between dilute aqueous HCl and EtOAc
  4. washThe organic solution was washed with water and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. filtrationfiltered
  8. customdried the solid

出典と根拠

ORDレコード
ord-901e22e0d9f641d085bcc34bac1ae3ec
出典データセット
uspto-grants-2014_06
特許番号
US08741887B2

反応ノート

読み込み中…