Potassium Acetate → 2,4-Difluoro-3-(pyridin-3-yl)benzeneboronic acid

HRID 2183932ノート

反応式

HRID 2183932 の反応式
Br[C:2]1[C:3]([F:15])=[C:4]([C:9]2[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=2)[C:5]([F:8])=[CH:6][CH:7]=1.C([O-])(=O)C.[K+].[B:21]1(B2OCC(C)(C)CO2)[O:26]CC(C)(C)C[O:22]1>O1CCOCC1>[F:15][C:3]1[C:4]([C:9]2[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=2)=[C:5]([F:8])[CH:6]=[CH:7][C:2]=1[B:21]([OH:26])[OH:22]

参加物

5

反応物 3

HCID 517044Potassium AcetateHCID 2734316Bis(neopentyl glycolato)diboronHCID 222400863-(3-Bromo-2,6-difluorophenyl)pyridine

生成物 1

HCID 222400962,4-Difluoro-3-(pyridin-3-yl)benzeneboronic acid収率 85.1%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
90 °C

実験手順

A mixture of 3-(3-bromo-2,6-difluorophenyl)pyridine (2.97 g, 11 mmol), potassium acetate (2.16 g, 22 mmol) and bis(neopentyl glycolato)diboron (2.86 g, 12.7 mmol) in 1,4-dioxane (30 ml) was heated at 90° C. for 16 h. The reaction was cooled, filtered (washing the filter cake with a small quantity of diethyl ether) and the filtrate concentrated in vacuo. The residue was partitioned between diethyl ether (100 ml) and 1M sodium hydroxide (100 ml) and the organics discarded. The aqueous was washed with more diethyl ether and then cooled in an ice-water bath. The pH was adjusted to approximately 6 with 36% hydrochloric acid, and allowed to stand for 1 h. The resulting solid was collected by filtration and dried under vacuum to afford 2,4-difluoro-3-(pyridin-3-yl)benzeneboronic acid (2.2 g, 85%) as a grey solid: m/z (ES+) 236 (M++H).

後処理

  1. temperatureThe reaction was cooled
  2. filtrationfiltered (
  3. washwashing the filter cake with a small quantity of diethyl ether) and the filtrate
  4. concentrationconcentrated in vacuo
  5. customThe residue was partitioned between diethyl ether (100 ml) and 1M sodium hydroxide (100 ml)
  6. washThe aqueous was washed with more diethyl ether
  7. temperaturecooled in an ice-water bath
  8. filtrationThe resulting solid was collected by filtration
  9. customdried under vacuum

出典と根拠

ORDレコード
ord-55487be94dd14405850fedc9b86e69d3
出典データセット
uspto-grants-2005_05
特許番号
US06900215B2

反応ノート

読み込み中…