4-Fluorobenzyl bromide → 2-(5-(4-Fluoro-benzyl)-furan-2-yl)-[1,3]dioxolane

HRID 78244

반응식

HRID 78244 반응식
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[O:7][CH:8]=[CH:9][CH:10]=1.C([Li])CCC.[F:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21]Br)=[CH:19][CH:18]=1>O1CCCC1>[F:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21][C:8]2[O:7][C:6]([CH:2]3[O:3][CH2:4][CH2:5][O:1]3)=[CH:10][CH:9]=2)=[CH:19][CH:18]=1

참가 물질

5

반응물 3

HCID 680214-Fluorobenzyl bromideHCID 2631582-Furyl-1,3-dioxolaneHCID 178418339Butyllithium

생성물 1

HCID 592550712-(5-(4-Fluoro-benzyl)-furan-2-yl)-[1,3]dioxolane수율 51%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a tetrahydrofuran (50 mL) solution of 2-(1,3-dioxolan-2-yl-furan (5 g, 35.7 mmol) was added n-butyl lithium (15.6 mL, 2.64 M hexane solution, 41.1 mmol) at −78° C., which was stirred for 1 hour at that temperature. A tetrahydrofuran solution of 4-fluorobenzyl bromide (6.9 g, 36.5 mmol) was added dropwise to this mixture, which was stirred for another hour at −78° C. The mixture was raised to room temperature and partitioned into ethyl acetate and a saturated ammonium chloride aqueous solution. The organic layer was separated, washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under a reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate:heptane=1:10 to 1:3) to obtain the title compound (4.51 g, 51%).

후처리

  1. stirringwas stirred for another hour at −78° C
  2. custompartitioned into ethyl acetate
  3. customThe organic layer was separated
  4. washwashed with saturated aqueous sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under a reduced pressure
  8. customthe residue was purified by silica gel column chromatography (ethyl acetate:heptane=1:10 to 1:3)

출처 및 근거

ORD 기록
ord-ec9e12fe4aab477799439ea67d534541
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841327B2

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