Acetic Acid → 3-Bromodibenzofuran

HRID 1022354ノート

反応式

HRID 1022354 の反応式
N([O-])=O.[Na+].N[C:6]1[CH:18]=[CH:17][C:9]2[O:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[C:8]=2[CH:7]=1.C(O)(=O)C.CCOCC.[BrH:28]>OS(O)(=O)=O.C(Cl)Cl.CCCCCC>[Br:28][C:18]1[CH:6]=[CH:7][C:8]2[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[O:10][C:9]=2[CH:17]=1

参加物

8

反応物 5

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 3283Diethyl EtherHCID 194052-DibenzofuranamineHCID 23668193Sodium Nitrite

生成物 1

HCID 2968613-Bromodibenzofuran

試薬・触媒・溶媒 2

HCID 1118Sulfuric Acid溶媒HCID 21226440Methylenechloride Hexane溶媒

反応条件

温度
0 °C

実験手順

NaNO2 (2.21 g, 32.05 mmol) was dissolved in 20 mL conc. H2SO4 in conical flask kept at 0° C. Solution of 2-aminodibenzofuran (5.3 g, 28.9 mmol) in minimum volume of glacial acetic acid was then slowly added to the flask so that temperature never raised above 5-8° C. and the mixture was stirred at 0° C. for another 1.5 h. 100 mL ether was added to the stirred mixture and precipitate of corresponding diazo salt immediately settled down. Brown color diazo salt was immediately filtered out and transferred to a flask containing CuBr (6.25 g, 43.5 mmol) in 150 mL 48% HBr. The flask was then placed in a water bath maintained at 64° C. and stirred for 2 h. After cooling down to room temperature, the dark color reaction content was filtered out and the precipitate was washed with water twice. Isolated solid was then flashed over Silica gel column with 5-10% DCM/Hexane to give 4.79 g final compound.

後処理

  1. customkept at 0° C
  2. filtrationBrown color diazo salt was immediately filtered out
  3. customtransferred to a flask
  4. customThe flask was then placed in a water bath
  5. temperaturemaintained at 64° C.
  6. stirringstirred for 2 h
  7. temperatureAfter cooling down to room temperature
  8. customthe dark color reaction content
  9. filtrationwas filtered out
  10. washthe precipitate was washed with water twice
  11. customIsolated solid

出典と根拠

ORDレコード
ord-3b9d2d8181fb4f66a0906c8428c6653c
出典データセット
uspto-grants-2014_05
特許番号
US08722205B2

反応ノート

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