Hydrochloric Acid → (2,2-dimethyl-2H-chromen-6-yl)boronic acid

HRID 1718514노트

반응식

HRID 1718514 반응식
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][C:7]([CH3:13])([CH3:12])[CH:6]=[CH:5]2.C([Li])CCC.[B:19](OC(C)C)([O:24]C(C)C)[O:20]C(C)C.Cl>O1CCCC1>[CH3:12][C:7]1([CH3:13])[CH:6]=[CH:5][C:4]2[C:9](=[CH:10][CH:11]=[C:2]([B:19]([OH:24])[OH:20])[CH:3]=2)[O:8]1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 21531Triisopropyl borateHCID 117705336-Bromo-2,2-dimethyl-2H-chromeneHCID 178418339Butyllithium

생성물 1

HCID 17750385(2,2-dimethyl-2H-chromen-6-yl)boronic acid수율 82%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 6-bromo-2,2-dimethyl-2H-chromene (18 g) in tetrahydrofuran (150 mL) was added butyllithium (53 mL, 1.6 M hexane solution) at −78° C. under an argon atmosphere, and the mixture was stirred for 30 min. Triisopropyl borate (21 mL) was added, and the mixture was stirred for 3 hr while allowing to warm to room temperature. 1 M hydrochloric acid (150 mL) was added to the reaction mixture, and the mixture was stirred for 2 hr and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, and the solvent was evaporated. The residue was purified by silica gel column chromatography to give the title compound (13 g, 82%) as colorless crystals.

후처리

  1. stirringthe mixture was stirred for 3 hr
  2. stirringthe mixture was stirred for 2 hr
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated
  7. customThe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-e4a9942df8f1439a8805d772f1b2c1d6
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07803940B2

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