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

HRID 1061776ノート

反応式

HRID 1061776 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 1 M 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 1 M 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-edf0cb496af541afa39827811846e7f2
出典データセット
uspto-grants-2005_11
特許番号
US06960598B2

反応ノート

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