Dichloromethane → N,N,4-Triethyl-2-fluorobenzamide

HRID 2100612ノート

反応式

HRID 2100612 の反応式
Br[C:2]1[CH:14]=[CH:13][C:5]([C:6]([N:8]([CH2:11][CH3:12])[CH2:9][CH3:10])=[O:7])=[C:4]([F:15])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:22]([Zn]CC)[CH3:23].ClCCl>CN(C=O)C.C1(C)C=CC=CC=1.C(OCC)(=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH2:9]([N:8]([CH2:11][CH3:12])[C:6](=[O:7])[C:5]1[CH:13]=[CH:14][C:2]([CH2:22][CH3:23])=[CH:3][C:4]=1[F:15])[CH3:10]

参加物

9

反応物 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 246940264-Bromo-N,N-diethyl-2-fluorobenzamideHCID 178418750HCID 178418750、化合物

生成物 1

HCID 69055558N,N,4-Triethyl-2-fluorobenzamide収率 88%

試薬・触媒・溶媒 4

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 1140Toluene溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

To a solution of 4-bromo-N,N-diethyl-2-fluorobenzamide (5.12 g, 18.9 mmol) in 100 mL of DMF was added potassium carbonate (6.45 g, 46.7 mmol) and diethylzinc (25.5 mL of a 1.1 M solution in toluene, 28.02 mmol). The solution was degassed with a stream of argon and then there was added [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II) complex with dichloromethane (1:1) (305 mg, 0.37 mmol). The reaction mixture was allowed to stir at 80° C. for 3 h. The reaction mixture was allowed to cool and was diluted with ethyl acetate. The organics were washed with water and brine, dried (MgSO4) and concentrated. The residue was purified (ISCO, elution with 0-40% EtOAc/hexane, 40 min) to afford 3.70 g (88%) of the title compound as a colorless oil. LRMS (ESI): 224.2 (M+H)+.

後処理

  1. customThe solution was degassed with a stream of argon
  2. temperatureto cool
  3. washThe organics were washed with water and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe residue was purified
  7. wash(ISCO, elution with 0-40% EtOAc/hexane, 40 min)

出典と根拠

ORDレコード
ord-95297d6ca93c47a59f8ec56740b21ebb
出典データセット
uspto-grants-2009_08
特許番号
US07572805B2

反応ノート

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