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Hydrochloric Acid → 2-Methoxyphenylboronic acid

HRID 2061
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HRID 2061 반응식
C([Li])CCC.Br[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[O:13][CH3:14].[B:15](OC)([O:18]C)[O:16]C.Cl>O1CCCC1>[CH3:14][O:13][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=1[B:15]([OH:18])[OH:16]
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참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 8470Trimethyl borateHCID 113582-BromoanisoleHCID 178418339Butyllithium

생성물 1

HCID 27339582-Methoxyphenylboronic acid수율 100.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

n-Butyl lithium (13.0 ml of a 1.6M solution in hexanes, 19.8 mmol) was added dropwise to a solution of 2-bromoanisole (3.74 g, 19.0 mmol) in anhydrous tetrahydrofuran (15 ml) cooled to below -70° C., maintaining the temperature during the addition below -60° C. The solution was stirred for 20 minutes before the addition of trimethyl borate (5.9 ml, 57.0 mmol), and then stirred at below -70° C. for a further hour before warming to room temperature overnight. The reaction mixture was cooled to 0° C. acidified to pH 5.0 with 5% aqueous hydrochloric acid solution (25 ml), the resulting layers separated and the aqueous phase extracted with ethyl acetate (2×25 ml). The combined orgnic layers were washed with brine (25 ml), dried (MgSO4) and concentrated in vacuo to yield the title compound as a white solid (2.9 g, 97%) which was used without further purification.

후처리

  1. temperaturecooled to below -70° C.
  2. temperaturemaintaining the temperature
  3. additionduring the addition below -60° C
  4. temperatureThe reaction mixture was cooled to 0° C.
  5. customthe resulting layers separated
  6. extractionthe aqueous phase extracted with ethyl acetate (2×25 ml)
  7. washThe combined orgnic layers were washed with brine (25 ml)
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-2a3e93aba57f445fa9497b301fde8efd
출처 데이터셋
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05728695

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