Dichloromethane → 3-Fluoro-4-nitrobenzamide

HRID 450525

반응식

HRID 450525 반응식
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])[C:5]#[N:6].C([O-])([O-])=[O:14].[K+].[K+].C(N)(N)=O.OO.C(Cl)Cl>CC(C)=O.O.O>[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])[C:5]([NH2:6])=[O:14]

참가 물질

7

반응물 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 31294Carbamide PeroxideHCID 27833993-Fluoro-4-nitrobenzonitrile

생성물 1

HCID 114239673-Fluoro-4-nitrobenzamide

시약·촉매·용매 2

HCID 962Water용매HCID 18366337Propan-2-one--water (1/1)용매

실험 절차

To a stirred solution of 3-fluoro-4-nitrobenzonitrile (15 g, 90.3 mmol) and K2CO3 (25.03 g, 181.1 mmol) in 100 mL of acetone/water (4:1) was added urea hydrogen peroxide adduct (16.99 g, 180.6 mmol) and the reaction stirred overnight at ambient temperature. DCM (100 mL) and water (500 mL) were added to the reaction mixture, the solution partitioned and the organic layer separated. The aqueous layer was extracted with DCM (3×100 mL) and the combined organic portions, washed with brine (100 mL), filtered through Celite and passed through a PTFE separation frit. The solvent was concentrated in vacuo and the title compound obtained as an orange solid (10 g, 60% yield) after recrystallisation from EtOAc/petroleum ether (40-60° C.).

후처리

  1. customthe solution partitioned
  2. customthe organic layer separated
  3. extractionThe aqueous layer was extracted with DCM (3×100 mL)
  4. washthe combined organic portions, washed with brine (100 mL)
  5. filtrationfiltered through Celite
  6. custompassed through a PTFE separation frit
  7. concentrationThe solvent was concentrated in vacuo

출처 및 근거

ORD 기록
ord-1d984eff158d4793ba928d519ac80044
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08486953B2

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