2,5-Dichlorophenol → 4-(2,5-Dichlorophenoxy)-3-nitrobenzonitrile

HRID 1946847

반응식

HRID 1946847 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[OH:9].Cl[C:11]1[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][C:12]=1[N+:19]([O-:21])=[O:20].C([O-])([O-])=O.[K+].[K+]>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[O:9][C:11]1[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][C:12]=1[N+:19]([O-:21])=[O:20]

참가 물질

5

반응물 3

HCID 662,5-DichlorophenolHCID 11430Potassium CarbonateHCID 13655Benzonitrile, 4-chloro-3-nitro-

생성물 1

HCID 595489424-(2,5-Dichlorophenoxy)-3-nitrobenzonitrile수율 81.8%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

2,5-Dichlorophenol (17.86 g, 109.54 mmol) and 4-chloro-3-nitrobenzonitrile (10.00 g, 54.77 mmol) were combined with K2CO3 (37.85 g, 273.85 mmol) in THF (300 mL). The reaction mixture was refluxed for 48 hrs and then the solid was filtered over a bed of Celite. After rinsing the residue with copious amounts of DCM, the filtrate was concentrated to produce a yellow solid. The solid was triturated with minimal DCM and collected via vacuum filtration to yield compound 34 (13.84 g, 81.7% yield, 100.0% pure). 1H NMR (500 MHz, DMSO-d6): δ 8.73 (s, 1H), 8.12 (dd, J1=9 Hz, J2=2 Hz, 1H), 7.73 (d, J=9 Hz, 1H), 7.65 (d, J=2 Hz, 1H), 7.48 (dd, J1=9 Hz, J2=2 Hz, 1H), 7.21 (d, J=9 Hz, 1H).

후처리

  1. temperatureThe reaction mixture was refluxed for 48 hrs
  2. filtrationthe solid was filtered over a bed of Celite
  3. washAfter rinsing the residue with copious amounts of DCM
  4. concentrationthe filtrate was concentrated
  5. customto produce a yellow solid
  6. customThe solid was triturated with minimal DCM
  7. filtrationcollected via vacuum filtration

출처 및 근거

ORD 기록
ord-c6845f4a525f42d7a7b4b65c46ef0020
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08399456B2

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