1-Bromo-4-nitrobenzene → Diethyl(4-nitrophenyl)phosphonate

HRID 45638

반응식

HRID 45638 반응식
[PH:1](=[O:8])([O:5][CH2:6][CH3:7])[O:2][CH2:3][CH3:4].Br[C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=1>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[N+:16]([C:13]1[CH:14]=[CH:15][C:10]([P:1](=[O:8])([O:5][CH2:6][CH3:7])[O:2][CH2:3][CH3:4])=[CH:11][CH:12]=1)([O-:18])=[O:17]

참가 물질

5

반응물 2

HCID 114661-Bromo-4-nitrobenzeneHCID 178476833HCID 178476833, 화합물

생성물 1

HCID 284865Diethyl(4-nitrophenyl)phosphonate

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 1140Toluene용매

반응 조건

온도
90 °C

실험 절차

Into a 100-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of diethyl phosphonate (3.02 g, 21.88 mmol, 1.10 equiv) in toluene (10 mL), Pd(PPh3)4 (1.15 g, 1.00 mmol, 0.05 equiv), TEA (2.21 g, 21.88 mmol, 1.10 equiv), 1-bromo-4-nitrobenzene (4 g, 19.90 mmol, 1.00 equiv). The resulting solution was stirred for 15 h at 90° C. The solids were filtered out and the resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column and eluted with ethyl acetate/petroleum ether (1:2). This resulted in 3.53 g (68%) of diethyl 4-nitrophenylphosphonate as a yellow liquid.

후처리

  1. customInto a 100-mL 3-necked round-bottom flask purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. filtrationThe solids were filtered out
  4. concentrationthe resulting mixture was concentrated under vacuum
  5. washeluted with ethyl acetate/petroleum ether (1:2)
  6. customThis resulted in 3.53 g (68%) of diethyl 4-nitrophenylphosphonate as a yellow liquid

출처 및 근거

ORD 기록
ord-4dbb424e99c34821909e93b90abb7eb8
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08541448B2

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