Iodine → 2-(4-Fluorophenyl)bicyclo[2.2.1]heptan-2-ol

HRID 2368756노트

반응식

HRID 2368756 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][CH:3]=1.[Mg].II.[CH2:12]1[CH:16]2[CH2:17][C:18](=[O:19])[CH:14]([CH2:15]2)[CH2:13]1>C1COCC1>[F:8][C:5]1[CH:6]=[CH:7][C:2]([C:18]2([OH:19])[CH2:17][CH:16]3[CH2:15][CH:14]2[CH2:13][CH2:12]3)=[CH:3][CH:4]=1

참가 물질

6

반응물 4

HCID 807IodineHCID 99931-Bromo-4-fluorobenzeneHCID 10345Bicyclo(2.2.1)heptan-2-oneHCID 5462224Magnesium

생성물 1

HCID 222978332-(4-Fluorophenyl)bicyclo[2.2.1]heptan-2-ol

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

A mixture of 1-bromo-4-fluorobenzene (5.00 ml, 45.5 mmol), magnesium turnings (3.32 g, 137 mmol), and a few iodine crystals in 70 ml dry THF were vigorously stirred for 4 hours under the protection of nitrogen and cooling with ice/water. Norcamphor (5.00 g, 45.5 mmol) dissolved in 10 ml dry THF was added drop-wise, and the reaction was allowed to warm up to room temperature and stirred overnight. The reaction was carefully quenched with water and decanted from the excess magnesium turnings. The reaction mixture in THF and water was adjusted to pH 7 with 2N HCl solution and extracted with chloroform (3×50 ml). The extract was dried over anhydrous sodium sulfate and the solvent was removed by vacuum evaporator. This resulted in an alcohol intermediate (III) appearing as a faintly yellow oil (9.4 g, 99%).

후처리

  1. additionwas added drop-wise
  2. customThe reaction was carefully quenched with water
  3. customdecanted from the excess magnesium turnings
  4. extractionextracted with chloroform (3×50 ml)
  5. dry with materialThe extract was dried over anhydrous sodium sulfate
  6. customthe solvent was removed by vacuum evaporator

출처 및 근거

ORD 기록
ord-c8b90d6f30ee4db8823e25314d0fb032
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08703799B2

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