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Potassium Carbonate → 4-Bromo-2-fluoro-1-(4-propylcyclohexyl)benzene

HRID 718488
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HRID 718488 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5](OCC)=[C:4]([F:11])[CH:3]=1.BrC[CH:14]1[CH2:19][CH2:18][CH:17]([CH2:20][CH2:21][CH3:22])[CH2:16][CH2:15]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:14]2[CH2:19][CH2:18][CH:17]([CH2:20][CH2:21][CH3:22])[CH2:16][CH2:15]2)=[C:4]([F:11])[CH:3]=1
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참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 115575971-(Bromomethyl)-4-propyl-trans-cyclohexaneHCID 145169324-Bromo-1-ethoxy-2-fluorobenzene

생성물 1

HCID 680105874-Bromo-2-fluoro-1-(4-propylcyclohexyl)benzene수율 67.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Under a nitrogen atmosphere, a mixture of 4-bromo-2-fluoro-1-phenol (52) (10.8 g, 56.58 mmol), 1-(bromomethyl)-4-propylcyclohexane (60) (12.4 g, 56.58 mmol) and potassium carbonate (15.6 g, 112.9 mmol) was agitated at 80° C. for 5 hours in 100 mL of DMF. The reaction mixture was quenched with 100 mL of water, and extracted with 60 mL of toluene three times. Combined organic layers were washed with a 2N sodium hydroxide aqueous solution, water and saturated brine, and then dried over magnesium sulfate, and a solvent was distilled off by an evaporator. The residue was purified by silica gel column chromatography, and thus 4-bromo-2-fluoro-1-(4-propylcyclohexyl)benzene (61) (11.4 g, yield 61.2%) was obtained.

후처리

  1. customThe reaction mixture was quenched with 100 mL of water
  2. extractionextracted with 60 mL of toluene three times
  3. washCombined organic layers were washed with a 2N sodium hydroxide aqueous solution, water and saturated brine
  4. dry with materialdried over magnesium sulfate
  5. distillationa solvent was distilled off by an evaporator
  6. customThe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-a5273f2884544200b4c056813c64543d
출처 데이터셋
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09193908B2

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