Triisopropyl borate → 2-(2-Methoxyethyl)phenylboronic acid

HRID 2194885노트

반응식

HRID 2194885 반응식
[CH3:1][O:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1Br.C([Li])CCC.C([O:20][B:21](OC(C)C)[O:22]C(C)C)(C)C>C1COCC1>[CH3:1][O:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[B:21]([OH:22])[OH:20]

참가 물질

5

반응물 3

HCID 21531Triisopropyl borateHCID 51519972-Bromophenethyl methyl etherHCID 178418339Butyllithium

생성물 1

HCID 674459962-(2-Methoxyethyl)phenylboronic acid

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

To a solution of 2-(2-bromophenyl)ethyl methyl ether (V.2; 1 eq.) in THF (0.16M) at −78° C. was added n-butyllithium (2.5M; 1.1 eq.). The reaction mixture was stirred for 1 h at −78° C. then tri-iso-propylborate (1.2 eq.) was added and the final mixture was allowed to warm slowly to room temperature and stirred for 1 h. The reaction was quenched with the addition of aqueous HCl (1N) and extracted with EtOAc. The organic extract was washed with brine, dried over Na2SO4, filtered and concentrated to afford the desired material as a foam which was used as such.

후처리

  1. temperatureto warm slowly to room temperature
  2. stirringstirred for 1 h
  3. customThe reaction was quenched with the addition of aqueous HCl (1N)
  4. extractionextracted with EtOAc
  5. extractionThe organic extract
  6. washwas washed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated

출처 및 근거

ORD 기록
ord-db85cea7e1664d38b59e2ba904e6f4d2
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08334308B2

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