Potassium Carbonate → 3-(Pyridin-3-yl)benzoic acid

HRID 415295ノート

反応式

HRID 415295 の反応式
B([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7]([OH:9])=[O:8])(O)O.Br[C:14]1[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[N:16]1[CH:17]=[CH:18][CH:19]=[C:14]([C:4]2[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=2)[C:7]([OH:9])=[O:8])[CH:15]=1

参加物

7

反応物 3

HCID 11430Potassium CarbonateHCID 122863-BromopyridineHCID 27339573-Carboxyphenylboronic acid

生成物 1

HCID 27955753-(Pyridin-3-yl)benzoic acid収率 83.7%

試薬・触媒・溶媒 3

HCID 178418476HCID 178418476、化合物触媒HCID 962Water溶媒HCID 6342Acetonitrile溶媒

実験手順

To a solution of 3-boronobenzoic acid (1.5 g, 9 mmol) and 3-bromopyridine (1.5 g, 9.9 mmol) in acetonitrile (40 mL) and water (40 mL), potassium carbonate (5.5 g, 40 mmol), Bis(triphenylphosphine)palladium(II) chloride (400 mg, 0.37 mmol) was added. The mixture was stirred under reflux overnight. Then the hot suspension was filtered and concentrated to half of the original volume and washed with dichloromethane. The aquatic phase was adjusted to pH=3 with hydrochloric acid (1 M) and filtrated, washed with water. The residue was dried in vacuum to obtain 1.5 g of 3-(pyridin-3-yl)benzoic acid. Yield: 83%. LC-MS (ESI) m/z: 200 (M+1)+.

後処理

  1. temperatureunder reflux overnight
  2. filtrationThen the hot suspension was filtered
  3. concentrationconcentrated to half of the original volume
  4. washwashed with dichloromethane
  5. filtrationfiltrated
  6. washwashed with water
  7. customThe residue was dried in vacuum

出典と根拠

ORDレコード
ord-813d26f59d694dd4a16e97d2962e7b22
出典データセット
uspto-grants-2012_01
特許番号
US08088760B2

反応ノート

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