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Benzene, 1-bromo-3-nitro- → HCID 57942920, 화합물

HRID 1438105
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HRID 1438105 반응식
[C:1]([O:5][C:6]([N:8]1[CH:12]=[CH:11][CH:10]=[C:9]1B(O)O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[N+:16]([C:19]1[CH:20]=[C:21](Br)[CH:22]=[CH:23][CH:24]=1)([O-:18])=[O:17]>COCCOC.C([O-])([O-])=O.[Na+].[Na+].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:19]1[CH:24]=[C:23]([C:9]2[N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH:12]=[CH:11][CH:10]=2)[CH:22]=[CH:21][CH:20]=1)([O-:18])=[O:17]
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참가 물질

6

반응물 2

HCID 11457Benzene, 1-bromo-3-nitro-HCID 27343211-(tert-Butoxycarbonyl)-2-pyrroleboronic Acid

생성물 1

HCID 57942920HCID 57942920, 화합물수율 76.3%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 80711,2-Dimethoxyethane용매
HCID 10340
Sodium Carbonate
용매

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온도
90 °C

실험 절차

A mixture of 3A (1.46 g, 6.9 mmol) and 3-nitrobromobenzene (0.81 g, 4.0 mmol) in DME (40 mL) and 2.0 M Na2CO3 (8.0 mL) was degassed by bubbling argon for 5 min. To this solution, Pd(PPh3)4 (280 mg, 0.25 mmol) was added. The mixture was heated at 90° C. for 5 h. After cooling to rt, it was extracted with EtOAc and dried over Na2SO4. The product was purified by silica gel chromatography (CH2Cl2/hexanes=1/5) to give 4A (880 mg, 75% yield) as viscous oil. 1H NMR (400 MHz, Methanol-d4) δ ppm 1.37 (s, 9H) 6.28 (t, J=3.52 Hz, 1H) 6.33 (dd, J=3.52, 1.76 Hz, 1H) 7.41 (dd, J=3.52, 1.76 Hz, 1H) 7.59 (m, 1H) 7.73 (d, J=7.91 Hz, 1H) 8.16 (m, 2H).

후처리

  1. customwas degassed
  2. customby bubbling argon for 5 min
  3. temperatureAfter cooling to rt
  4. extractionit was extracted with EtOAc
  5. dry with materialdried over Na2SO4
  6. customThe product was purified by silica gel chromatography (CH2Cl2/hexanes=1/5)

출처 및 근거

ORD 기록
ord-1fc8eb0dbef2420ba32eea31984c233c
출처 데이터셋
uspto-grants-2009_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07622585B2

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