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

HRID 2100612노트

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HRID 2100612 반응식
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]

참가 물질

9

반응물 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 246940264-Bromo-N,N-diethyl-2-fluorobenzamideHCID 178418750HCID 178418750, 화합물

생성물 1

HCID 69055558N,N,4-Triethyl-2-fluorobenzamide수율 88%

시약·촉매·용매 4

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 1140Toluene용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

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온도
80 °C

실험 절차

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)+.

후처리

  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)

출처 및 근거

ORD 기록
ord-95297d6ca93c47a59f8ec56740b21ebb
출처 데이터셋
uspto-grants-2009_08
특허 번호
US07572805B2

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