Potassium Carbonate → 2-Nitrobiphenyl-4-carbaldehyde

HRID 659644

反応式

HRID 659644 の反応式
Br[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].[C:13]1(B(O)O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1.O.CCOCC.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+:10]([C:3]1[CH:4]=[C:5]([CH:6]=[O:7])[CH:8]=[CH:9][C:2]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([O-:12])=[O:11]

参加物

8

反応物 3

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 8087924-Bromo-3-nitrobenzaldehyde

生成物 1

HCID 118170112-Nitrobiphenyl-4-carbaldehyde収率 59%

試薬・触媒・溶媒 4

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 1140Toluene溶媒HCID 3283Diethyl Ether溶媒

反応条件

温度
110 °C

実験手順

A 250-mL 3-necked round-bottom flask was charged with a solution of 4-bromo-3-nitrobenzaldehyde (11.5 g, 50.00 mmol, 1.00 equiv) in toluene (80 mL). To this was added phenylboronic acid (6.7 g, 54.92 mmol, 1.10 equiv), followed by the addition of a solution of K2CO3 (13.8 g, 100.00 mmol, 2.00 equiv) in water (50 mL). To the mixture was added Pd(PPh3)4 (1.2 g, 1.04 mmol, 0.02 equiv) in one portion. The resulting solution was stirred at 110° C. for 15 hours. Upon completion, the reaction mixture was cooled down to room temperature. The resulting solution was diluted with 1000 mL of Et2O. The solids were filtered out. The resulting organic layers were washed with water (3×300 mL), dried over anhydrous magnesium sulfate and concentrated on a rotary evaporator. The residue was purified by silica gel column chromatography eluted with ethyl acetate/petroleum ether (1:50) to afford 2-nitrobiphenyl-4-carbaldehyde as yellow solid (6.7 g, 59%).

後処理

  1. temperatureUpon completion, the reaction mixture was cooled down to room temperature
  2. filtrationThe solids were filtered out
  3. washThe resulting organic layers were washed with water (3×300 mL)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated on a rotary evaporator
  6. customThe residue was purified by silica gel column chromatography
  7. washeluted with ethyl acetate/petroleum ether (1:50)

出典と根拠

ORDレコード
ord-da6cabbcd9664aa89d67532b7809f520
出典データセット
uspto-grants-2011_12
特許番号
US08080566B1

関連ノート

読み込み中…