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

HRID 1816283

反応式

HRID 1816283 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

HCID 123772252-(2-Nitrophenyl)furan収率 27%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 6228Dimethylformamide溶媒

実験手順

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.]

後処理

  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

出典と根拠

ORDレコード
ord-3261a5a25f3f4ce8b425debab6f21333
出典データセット
uspto-grants-2005_04
特許番号
US06884801B1

関連ノート

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