1-Bromo-2-nitrobenzene → 2-(2-Nitrophenyl)furan

HRID 1816283

반응식

HRID 1816283 반응식
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1Br)([O-:3])=[O:2].C([Sn](CCCC)(CCCC)[C:16]1[O:17][CH:18]=[CH:19][CH:20]=1)CCC>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.CN(C=O)C>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:16]1[O:17][CH:18]=[CH:19][CH:20]=1)([O-:3])=[O:2]

참가 물질

5

반응물 2

HCID 113411-Bromo-2-nitrobenzeneHCID 43936882-(Tributylstannyl)furan

생성물 1

HCID 123772252-(2-Nitrophenyl)furan수율 27%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 6228Dimethylformamide용매

실험 절차

A DMF solution of 2-nitrobromobenzene (2.02 g), 2-tributylstannylfuran (3.31 mL), and tetrakis(triphenylphosphine)palladium was heated at 97° C. under N2 overnight. The mixture was evaporated to a small volume. The residue was suspended in 40 mL of water. This mixture was extracted with two 50 mL portions of Et2O. The combined extracts were dried and evaporated. This oil was purified by chromatography on silica gel with 10% EtOAc/hexanes to yield 0.51 g (27%) of 2-(2-nitrophenyl)furan. [This compound was reported in Smith et al.; J. Am. Chem. Soc. 1953, 75, 6335.]

후처리

  1. customThe mixture was evaporated to a small volume
  2. extractionThis mixture was extracted with two 50 mL portions of Et2O
  3. customThe combined extracts were dried
  4. customevaporated
  5. customThis oil was purified by chromatography on silica gel with 10% EtOAc/hexanes

출처 및 근거

ORD 기록
ord-3261a5a25f3f4ce8b425debab6f21333
출처 데이터셋
uspto-grants-2005_04
특허 번호
US06884801B1

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