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

HRID 409898노트

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HRID 409898 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 10d (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 triturated with CH2Cl2, filtered and the solid dried to give compound 10e (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. customThe residue was triturated with CH2Cl2
  8. filtrationfiltered
  9. customthe solid dried

출처 및 근거

ORD 기록
ord-53e967530a104946aaf26fe7aace3a86
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08759533B2

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