Sodium Carbonate → 2-(4'-Benzoylphenyl)-5-bromopyridine

HRID 1912222ノート

反応式

HRID 1912222 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.[C:9]([C:17]1[CH:22]=[CH:21][C:20](B(O)O)=[CH:19][CH:18]=1)(=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(=O)([O-])[O-].[Na+].[Na+]>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.C1(C)C=CC=CC=1>[C:9]([C:17]1[CH:22]=[CH:21][C:20]([C:2]2[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=2)=[CH:19][CH:18]=1)(=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 693532,5-DibromopyridineHCID 41972354-Benzoylbenzeneboronic acid

生成物 1

HCID 591563002-(4'-Benzoylphenyl)-5-bromopyridine収率 13.4%

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
90 °C

実験手順

2,5-dibromopyridine (15.85 g, 66.0 mmol) was weighed into a reaction vessel in an argon stream and prepared into a solution by the addition of toluene (300 mL). 4-benzoylphenylboronic acid (18.86 g, 83.0 mmol), tetrakis(triphenylphosphine)palladium(0) (3.05 g, 2.6 mmol) and a 1.41 M aqueous sodium carbonate solution (100 mL) were added thereto, and the mixture was stirred at 90° C. for 8 hours. From the obtained reaction mixture, the solid was collected by filtration. This solid was washed with cold toluene and cold diethyl ether in this order. This solid was dissolved in a toluene/chloroform mixed solvent (volume ratio: 2/1) and purified by silica gel column chromatography. The eluate was evaporated to dryness, and the obtained residue was dissolved in a chloroform/ethanol mixed solvent (volume ratio: 9/2) and recrystallized several times to obtain 2-(4′-benzoylphenyl)-5-bromopyridine (3.00 g, 8.87 mmol) as a yellow solid.

後処理

  1. customFrom the obtained reaction mixture
  2. filtrationthe solid was collected by filtration
  3. washThis solid was washed with cold toluene and cold diethyl ether in this order
  4. dissolutionThis solid was dissolved in a toluene/chloroform mixed solvent (volume ratio: 2/1)
  5. custompurified by silica gel column chromatography
  6. customThe eluate was evaporated to dryness
  7. dissolutionthe obtained residue was dissolved in a chloroform/ethanol mixed solvent (volume ratio: 9/2)
  8. customrecrystallized several times

出典と根拠

ORDレコード
ord-f1199cbf64a74216b82c39c34a79a36c
出典データセット
uspto-grants-2013_12
特許番号
US08608986B2

反応ノート

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