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

HRID 401684노트

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HRID 401684 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
-70 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-901e22e0d9f641d085bcc34bac1ae3ec
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08741887B2

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