Hydrochloric Acid → (4-Cyclopropoxyphenyl)boronic acid

HRID 646152노트

반응식

HRID 646152 반응식
Br[C:2]1([O:8][CH:9]2[CH2:11][CH2:10]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH2:3]1.[Li]CCCC.[B:17](OCC)([O:21]CC)[O:18]CC.Cl>C1COCC1>[CH:9]1([O:8][C:2]2[CH:7]=[CH:6][C:5]([B:17]([OH:21])[OH:18])=[CH:4][CH:3]=2)[CH2:11][CH2:10]1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 9009Triethyl borateHCID 686990414-Bromo-4-cyclopropoxybenzeneHCID 178418339Butyllithium

생성물 1

HCID 53216708(4-Cyclopropoxyphenyl)boronic acid수율 36%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 4-bromo-4-cyclopropoxybenzene (5.0 g, 23.4 mmol, see Example 39(c)) in THF (80 mL) at −78° C. was added n-BuLi (2.5 M solution in hexane; 9.76 mL, 24.4 mmol) over 17 min. After 40 min, B(OEt)3 (5.9 mL, 34.3 mmol) was added and the reaction was warmed to room temperature and stirred at ambient temperature for 18 h. After re-cooling to 0° C., HCl (1M solution; 70 mL, aq.) was added. After 30 min the mixture was extracted with t-BuOMe (3×50 mL), the combined organic extracts were washed with brine, dried (Na2SO4) and concentrated. The residue was washed with light petrol and filtered yielding the sub-title compound (1.5 g, 34%).

후처리

  1. temperatureAfter re-cooling to 0° C.
  2. extractionAfter 30 min the mixture was extracted with t-BuOMe (3×50 mL)
  3. washthe combined organic extracts were washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. washThe residue was washed with light petrol
  7. filtrationfiltered

출처 및 근거

ORD 기록
ord-821109ee1aad4d8490dc0337242d8313
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07705023B2

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