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Isopropanol → 3-Chloro-4-ethoxy-2-fluoro-4'-(4-propylcyclohexa-1-enyl)biphenyl

HRID 641102
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HRID 641102 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][CH3:16])[CH2:10][CH:9]=2)=[CH:4][CH:3]=1.[Cl:17][C:18]1[C:19]([F:30])=[C:20](B(O)O)[CH:21]=[CH:22][C:23]=1[O:24][CH2:25][CH3:26].C(=O)([O-])[O-].[K+].[K+].CC(O)C>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O.C1(C)C=CC=CC=1>[Cl:17][C:18]1[C:19]([F:30])=[C:20]([C:2]2[CH:3]=[CH:4][C:5]([C:8]3[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][CH3:16])[CH2:10][CH:9]=3)=[CH:6][CH:7]=2)[CH:21]=[CH:22][C:23]=1[O:24][CH2:25][CH3:26]
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참가 물질

8

반응물 4

HCID 3776IsopropanolHCID 11430Potassium CarbonateHCID 51358177(3-Chloro-4-ethoxy-2-fluorophenyl)boronic acidHCID 543121671-Bromo-4-(4-propylcyclohexa-1-enyl)benzene

생성물 1

HCID 592572253-Chloro-4-ethoxy-2-fluoro-4'-(4-propylcyclohexa-1-enyl)biphenyl수율 73.6%

시약·촉매·용매 3

HCID 178418476
HCID 178418476, 화합물
촉매
HCID 962Water용매
HCID 1140Toluene용매

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온도
25 °C

실험 절차

6.0 g of the compound (16), 5.5 g of the compound (12), 5.9 g of potassium carbonate and 0.13 g of Pd(PPh3)2Cl2 were added to a reactor having 60 mL of IPA placed therein under nitrogen atmosphere. The mixture was stirred under refluxing and heating for 3 hours. After cooling the reaction mixture to 25° C., 200 mL of toluene and 200 mL of water were added thereto, and the resulting toluene solution was washed with a 2N sodium hydroxide aqueous solution, a saturated sodium bicarbonate aqueous solution and water. Thereafter, the solvent was removed by distillation to obtain a residue. The resulting residue was purified by recrystallization from a mixed solvent of toluene and ethyl acetate (toluene/ethyl acetate=1/1 by volume). The resulting crystals were purified by silica gel column chromatography using toluene as eluent, and then further purified by recrystallization from a mixed solvent of heptane and ethanol (heptane/ethanol=5/1 by volume) to obtain 5.9 g of 3-chloro-4-ethoxy-2-fluoro-4′-(4-propylcyclohexa-1-enyl)biphenyl (No. 130). The resulting compound (No. 130) was colorless crystals. The yield based on the compound (13) was 45.0%.

후처리

  1. temperatureunder refluxing
  2. temperatureheating for 3 hours
  3. washthe resulting toluene solution was washed with a 2N sodium hydroxide aqueous solution
  4. customThereafter, the solvent was removed by distillation
  5. customto obtain a residue
  6. customThe resulting residue was purified by recrystallization from a mixed solvent of toluene and ethyl acetate (toluene/ethyl acetate=1/1 by volume)
  7. customThe resulting crystals were purified by silica gel column chromatography
  8. customfurther purified by recrystallization from a mixed solvent of heptane and ethanol (heptane/ethanol=5/1 by volume)

출처 및 근거

ORD 기록
ord-df30d6a4f9384b35b67a18f1be6cb7f9
출처 데이터셋
uspto-grants-2010_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07695777B2

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