Dichloromethane → 3-Fluoro-4-nitrobenzamide

HRID 450525ノート

反応式

HRID 450525 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

HCID 114239673-Fluoro-4-nitrobenzamide

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 18366337Propan-2-one--water (1/1)溶媒

実験手順

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.).

後処理

  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

出典と根拠

ORDレコード
ord-1d984eff158d4793ba928d519ac80044
出典データセット
uspto-grants-2013_07
特許番号
US08486953B2

反応ノート

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