Ethanol → 3-Nitro-4'-(pyrrolidine-1-carbonyl)biphenyl-4-carbaldehyde

HRID 37983

反応式

HRID 37983 の反応式
Br[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([N+:10]([O-:12])=[O:11])[CH:3]=1.[N:13]1([C:18]([C:20]2[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][CH:21]=2)=[O:19])[CH2:17][CH2:16][CH2:15][CH2:14]1.CCO.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.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:4]1[CH:3]=[C:2]([C:23]2[CH:22]=[CH:21][C:20]([C:18]([N:13]3[CH2:14][CH2:15][CH2:16][CH2:17]3)=[O:19])=[CH:25][CH:24]=2)[CH:9]=[CH:8][C:5]=1[CH:6]=[O:7])([O-:12])=[O:11]

参加物

7

反応物 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 6080994-Bromo-2-nitrobenzaldehydeHCID 2773571(4-(Pyrrolidine-1-carbonyl)phenyl)boronic acid

生成物 1

HCID 866526783-Nitro-4'-(pyrrolidine-1-carbonyl)biphenyl-4-carbaldehyde収率 178.9%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 1140Toluene溶媒

反応条件

温度
100 °C

実験手順

To a solution of 4-bromo-2-nitrobenzaldehyde (20.2 g, 87.9 mmol), 4-(pyrrolidine-1-carbonyl)phenylboronic acid (21.2 g, 96.7 mmol), and Pd(PPh3)4 (508 mg, 0.440 mmol) in toluene (200 mL) was added EtOH (40 mL) followed by Na2CO3 (70.0 mL, 140 mmol, 2 M aq solution) at room temperature. The resulting mixture was heated at 100° C. for 18 h. The reaction mixture was cooled to room temperature and the organic layer was separated. The aqueous layer was extracted with EtOAc (300 mL). The combined organic layers were washed with brine (500 mL), dried over MgSO4, filtered, and concentrated under reduced pressure to give the crude material that was combined with another batch of the crude material obtained from an additional run in the same reaction scale. The combined crude material was purified by silica gel flash column chromatography (CH2Cl2 to 1% MeOH in CH2Cl2) to afford 51 g (90%) of 3-nitro-4′-(pyrrolidine-1-carbonyl)biphenyl-4-carbaldehyde.

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customthe organic layer was separated
  3. extractionThe aqueous layer was extracted with EtOAc (300 mL)
  4. washThe combined organic layers were washed with brine (500 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto give the crude material that
  9. customobtained from an additional run in the same reaction scale
  10. customwas purified by silica gel flash column chromatography (CH2Cl2 to 1% MeOH in CH2Cl2)

出典と根拠

ORDレコード
ord-27e544011cbf49da991097b64d7aaf09
出典データセット
uspto-grants-2013_09
特許番号
US08524702B2

関連ノート

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