Trimethyl borate → 3-Ethoxy-4-fluorobenzeneboronic acid

HRID 1515507

반응식

HRID 1515507 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[C:4]([O:9][CH2:10][CH3:11])[CH:3]=1.[Li]CCCC.[B:17](OC)([O:20]C)[O:18]C>C1COCC1>[CH2:10]([O:9][C:4]1[CH:3]=[C:2]([B:17]([OH:20])[OH:18])[CH:7]=[CH:6][C:5]=1[F:8])[CH3:11]

참가 물질

5

반응물 3

HCID 8470Trimethyl borateHCID 598380294-Bromo-2-ethoxy-1-fluorobenzeneHCID 178418339Butyllithium

생성물 1

HCID 445581743-Ethoxy-4-fluorobenzeneboronic acid수율 69%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 9A (3.86 g, 17.6 mmol) in THF (60 mL) at −78° C. was added n-BuLi (1.6 M in hexanes, 14.3 mL, 22.8 mmol). The mixture was stirred at −78° C. for 40 min before trimethyl borate (3.63 mL, 33 mmol) was added. The reaction was left stirring from −78° C. to rt over 4 h. It was quenched with 1.0 N HCl (40 mL), extracted with EtOAc, washed with brine and dried over Na2SO4. After evaporation of the solvent, the crude solid product was triturated with EtOAc/hexanes (1:4). After filtration, 9B (2.2 g, 69% yield) was collected as a white solid. 1H NMR (400 MHz, CDCl3) δ ppm 1.42 (t, J=7.03 Hz, 3H) 4.11 (q, J=7.03 Hz, 2H) 7.03 (dd, J=11.42, 8.35 Hz, 1H) 7.18-7.29 (m, 2H) 7.35 (d, J=7.91 Hz, 1H).

후처리

  1. additionwas added
  2. waitThe reaction was left
  3. customIt was quenched with 1.0 N HCl (40 mL)
  4. extractionextracted with EtOAc
  5. washwashed with brine
  6. dry with materialdried over Na2SO4
  7. customAfter evaporation of the solvent
  8. customthe crude solid product was triturated with EtOAc/hexanes (1:4)

출처 및 근거

ORD 기록
ord-f451a95260c146d8bd02c6da25e347df
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08222453B2

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