Methyl 2-bromo-4-methylbenzoate → 1-(2-Bromo-4-methylphenyl)cyclopentanol

HRID 1037031노트

반응식

HRID 1037031 반응식
[Br:1][C:2]1[CH:11]=[C:10]([CH3:12])[CH:9]=[CH:8][C:3]=1[C:4]([O:6]C)=O.[Mg]([CH2:15][CH2:16][CH2:17][CH2:18][Mg]Br)Br>C1COCC1>[Br:1][C:2]1[CH:11]=[C:10]([CH3:12])[CH:9]=[CH:8][C:3]=1[C:4]1([OH:6])[CH2:18][CH2:17][CH2:16][CH2:15]1

참가 물질

4

반응물 2

HCID 21779704Methyl 2-bromo-4-methylbenzoateHCID 178419681HCID 178419681, 화합물

생성물 1

HCID 726983321-(2-Bromo-4-methylphenyl)cyclopentanol수율 78%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of methyl 2-bromo-4-methylbenzoate (5.0 g, 21.3 mmol) in THF (20 mL) was added dropwise BrMg(CH2)4MgBr (50 mL, 25.5 mmol) at 0° C. under nitrogen and then stirred at rt overnight. The reaction mixture was quenched with aqueous NH4Cl and extracted with EA. The combined organic layer was washed with aqueous NaHCO3 solution and brine, dried over Na2SO4. The solution was concentrated and the residue was purified by column chromatography over silica gel eluted with PE-EA (20:1˜10:1) to provide 1-(2-bromo-4-methylphenyl)-cyclopentanol (4.2 g; yield 78%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 7.65 (d, 1 H), 7.39 (s, 1 H), 7.10 (d, 1 H), 4.84 (s, 1 H), 2.33 (s, 3 H), 1.89-1.74 (m, 8 H) ppm.

후처리

  1. customThe reaction mixture was quenched with aqueous NH4Cl
  2. extractionextracted with EA
  3. washThe combined organic layer was washed with aqueous NaHCO3 solution and brine
  4. dry with materialdried over Na2SO4
  5. concentrationThe solution was concentrated
  6. customthe residue was purified by column chromatography over silica gel
  7. washeluted with PE-EA (20:1˜10:1)

출처 및 근거

ORD 기록
ord-728f67e1f5384b7d8e5a250400a1ee1c
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08546357B2

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