Hydrochloric Acid → 2-Fluoropyridine-3-boronic acid

HRID 52132

反応式

HRID 52132 の反応式
[Li]CCCC.[F:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=1.[B:13](OC)([O:16]C)[O:14]C.Cl>C1COCC1.O.C1COCC1>[F:6][C:7]1[C:12]([B:13]([OH:16])[OH:14])=[CH:11][CH:10]=[CH:9][N:8]=1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 8470Trimethyl borateHCID 97462-FluoropyridineHCID 178418339Butyllithium

生成物 1

HCID 27832702-Fluoropyridine-3-boronic acid

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒3 回HCID 21881883Oxolane--water (1/1)溶媒

反応条件

温度
-78 °C

実験手順

800 ml (1.28 mol) of n-BuLi (1.6M in hexane) are added to a solution of 188 ml (1.32 mol) of TMP in 1,000 ml of THF at -78° C. under argon. After the mixture has been stirred for 45 minutes at this temperature, 120.4 g (1.24 mol) of 2-fluoropyridine in 200 ml of THF are added in the course of 3 minutes. After the mixture has been stirred for 4 hours at -78° C., a solution of 128.8 g (1.24 mol) of trimethyl borate in 200 ml of THF is added dropwise in the course of 20 minutes. Then, 200 ml of a 1: 1 mixture of water/THF is added at 25° C., and 256 ml of concentrated HCl are added dropwise, with ice-cooling. The organic phase is separated off, and the aqueous phase is washed twice using Et2O, filtered and concentrated in vacuo. Crude yield 148.2 g.

後処理

  1. additionare added in the course of 3 minutes
  2. additionis added at 25° C.
  3. temperaturecooling
  4. customThe organic phase is separated off
  5. washthe aqueous phase is washed twice using Et2O
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-795d1700bda843fc9c46358a5d1176d3
出典データセット
uspto-grants-1997_04
特許番号
US05616590

関連ノート

読み込み中…