Hydrochloric Acid → 4-(Benzyloxy)-2-vinylphenylboronic acid

HRID 1394836노트

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HRID 1394836 반응식
[B:1](OC(C)C)([O:6]C(C)C)[O:2]C(C)C.[CH2:14]([O:21][C:22]1[CH:27]=[CH:26][C:25](Br)=[C:24]([CH:29]=[CH2:30])[CH:23]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C([Li])CCC.Cl>C1COCC1.O>[CH2:14]([O:21][C:22]1[CH:27]=[CH:26][C:25]([B:1]([OH:6])[OH:2])=[C:24]([CH:29]=[CH2:30])[CH:23]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 21531Triisopropyl borateHCID 692072164-(Benzyloxy)-1-bromo-2-vinylbenzeneHCID 178418339Butyllithium

생성물 1

HCID 692054944-(Benzyloxy)-2-vinylphenylboronic acid수율 602.9%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

Triisopropyl borate (683 mg, 3.63 mmol) was added to a stirred solution of 4-(benzyloxy)-1-bromo-2-vinylbenzene (1.0 g, 0.346 mmol) in THF (9 mL). The solution was cooled in a CO2/acetone bath. A solution of n-butyllithium (1.45 mL of 2.5M in hexanes, 3.63 mmol) was added dropwise over 5 minutes. The cooling bath was left in place and was allowed to warm to room temperature. The mixture was treated with HCl (5 mL of 1N) and water (5 mL), stirred for 1 hour, and extracted with ethyl acetate (3×15 mL). The combined extracts were washed with brine, dried (MgSO4), filtered, and concentrated to an oil which crystallized from diethyl ether/hexanes to provide colorless crystals of the desired product (530 mg, 57% yield). 1H NMR (300 MHz, CDCl3) δ 5.14 (s, 2H), 5.34 (d, J=12.44 Hz, 1H), 5.68 (d, J=17.57 Hz, 1H), 6.97 (dd, J=8.42, 2.56 Hz, 1H), 7.36 (m, 6H), 7.83 (dd, J=17.57, 10.98 Hz, 1H), 8.16 (d, J=8.42 Hz, 1H).

후처리

  1. temperatureThe solution was cooled in a CO2/acetone bath
  2. waitThe cooling bath was left in place
  3. extractionextracted with ethyl acetate (3×15 mL)
  4. washThe combined extracts were washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated to an oil which
  8. customcrystallized from diethyl ether/hexanes

출처 및 근거

ORD 기록
ord-37aeb06a58e84ca9a906ada43bd60611
출처 데이터셋
uspto-grants-2008_03
특허 번호
US07348425B2

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