Hydrochloric Acid → 2-Fluoropyridine-3-boronic acid

HRID 52132

반응식

HRID 52132 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

HCID 27832702-Fluoropyridine-3-boronic acid

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매3회HCID 21881883Oxolane--water (1/1)용매

반응 조건

온도
-78 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-795d1700bda843fc9c46358a5d1176d3
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05616590

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