Triisopropyl borate → 2-Methoxy-5-(trifluoromethyl)phenylboronic acid

HRID 1994607노트

반응식

HRID 1994607 반응식
C([Li])CCC.I[C:7]1[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=[CH:9][C:8]=1[O:17][CH3:18].[B:19](OC(C)C)([O:24]C(C)C)[O:20]C(C)C>C1COCC1>[CH3:18][O:17][C:8]1[CH:9]=[CH:10][C:11]([C:13]([F:16])([F:15])[F:14])=[CH:12][C:7]=1[B:19]([OH:24])[OH:20]

참가 물질

5

반응물 3

HCID 21531Triisopropyl borateHCID 187062962-iodine-4 -(trifluoromethyl) anisoleHCID 178418339Butyllithium

생성물 1

HCID 27826762-Methoxy-5-(trifluoromethyl)phenylboronic acid

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

n-Butyl lithium (1.6M in hexanes, 456 μL, 0.729 mmol) was added dropwise to a stirred solution of 2-iodo-1-methoxy-4-(trifluoromethyl)benzene (Step A, 200 mg, 0.662 mmol) in THF (1.5 mL) at −78° C. under an atmosphere of nitrogen. The reaction stirred at −78° C. for 30 min prior to the addition of triisopropyl borate (458 μL, 1.986 mmol). The reaction stirred an additional 2 h at −78° C. and was quenched with sat. NH4Cl. The mixture was extracted with CH2Cl2 and the organic phase was washed with NaHCO3 (15 mL) and brine (15 mL), dried (Na2SO4), filtered, conc. in vacuo to afford [2-methoxy-5-(trifluoromethyl)phenyl] boronic acid which was carried on without purification.

후처리

  1. stirringThe reaction stirred an additional 2 h at −78° C.
  2. customwas quenched with sat. NH4Cl
  3. extractionThe mixture was extracted with CH2Cl2
  4. washthe organic phase was washed with NaHCO3 (15 mL) and brine (15 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered, conc. in vacuo

출처 및 근거

ORD 기록
ord-0412635863374b26869bb505e5c3d4c0
출처 데이터셋
uspto-grants-2010_01
특허 번호
US07652049B2

반응 노트

불러오는 중…