Water → 5-(3-Bromophenyl)-2-furaldehyde

HRID 446062

反応式

HRID 446062 の反応式
[CH:1]([C:3]1[O:7][C:6](B(O)O)=[CH:5][CH:4]=1)=[O:2].[Br:11][C:12]1[CH:13]=[C:14](I)[CH:15]=[CH:16][CH:17]=1.C(=O)([O-])[O-].[Na+].[Na+].O>COCCOC.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>[Br:11][C:12]1[CH:17]=[C:16]([C:6]2[O:7][C:3]([CH:1]=[O:2])=[CH:4][CH:5]=2)[CH:15]=[CH:14][CH:13]=1

参加物

7

反応物 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 11561Benzene, 1-bromo-3-iodo-HCID 27343555-Formylfuran-2-boronic acid

生成物 1

HCID 8405175-(3-Bromophenyl)-2-furaldehyde収率 25.9%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 80711,2-Dimethoxyethane溶媒

実験手順

5-Formyl-2-furanboronic acid (676 mg, 4.8 mmol) and 3-bromoiodobenzene (1132 mg, 4 mmol) were dissolved in 1,2-dimethoxyethane (30 mL), tetrakis(triphenylphosphine)palladium (228 mg, 0.2 mmol) was added thereto, 2 mol/L sodium carbonate (9.6 mL) was further added thereto, and the mixture was heated to reflux for 2 hours while stirring. After the reaction was completed water (20 mL) was added thereto, and extraction with ethyl acetate (20 mL×2) was carried out. The organic layer was washed with saturated brine, water was removed using anhydrous sodium sulfate, the solvent was then removed by evaporation under reduced pressure, and the residue was subjected to silica gel column chromatography using ethyl acetate/hexane (3/7 (volume ratio)) as an eluent, to give 5-(3-bromophenyl)furan-2-carbaldehyde in a yield of 306 mg (yield 25.9%).

後処理

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 2 hours
  3. additionwas added
  4. extractionextraction with ethyl acetate (20 mL×2)
  5. washThe organic layer was washed with saturated brine, water
  6. customwas removed
  7. customthe solvent was then removed by evaporation under reduced pressure

出典と根拠

ORDレコード
ord-5e7c749d4a9446d4a9a263f8c69dd32d
出典データセット
uspto-grants-2013_07
特許番号
US08476449B2

関連ノート

読み込み中…