Isopropanol → 3-Fluoro-4'-(4-propylcyclohexyl)biphenyl-4-ol

HRID 1912235

반응식

HRID 1912235 반응식
[CH2:1]([CH:4]1[CH2:9][CH2:8][CH:7]([C:10]2[CH:15]=[CH:14][C:13](B(O)O)=[CH:12][CH:11]=2)[CH2:6][CH2:5]1)[CH2:2][CH3:3].[F:19][C:20]1[CH:25]=[C:24](Br)[CH:23]=[CH:22][C:21]=1[OH:27].C(=O)([O-])[O-].[K+].[K+].C(O)(C)C>O>[F:19][C:20]1[CH:25]=[C:24]([C:13]2[CH:12]=[CH:11][C:10]([CH:7]3[CH2:8][CH2:9][CH:4]([CH2:1][CH2:2][CH3:3])[CH2:5][CH2:6]3)=[CH:15][CH:14]=2)[CH:23]=[CH:22][C:21]=1[OH:27]

참가 물질

6

반응물 4

HCID 3776IsopropanolHCID 11430Potassium CarbonateHCID 27249814-Bromo-2-fluorophenolHCID 31047104-(trans-4-Propylcyclohexyl)phenylboronic Acid

생성물 1

HCID 585684903-Fluoro-4'-(4-propylcyclohexyl)biphenyl-4-ol수율 55.2%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
70 °C

실험 절차

Dichlorobistriphenylphosphinepalladium (0.143 g) was added to a mixture of 4-(4-propylcyclohexyl)phenylboronic acid (10.0 g), 2-fluoro-4-bromophenol (7.76 g), potassium carbonate (11.2 g) and isopropyl alcohol (90 ml) under a stream of nitrogen, and the mixture was heated to reflux at 70° C. for 4 hours. The reaction mixture was poured into water, which was extracted with diethyl ether. The extract was washed with water three times and the solvent was distilled off. The residue was purified by silica gel-column chromatography (solvent: toluene/ethyl acetate=10/1 by volume), and then by recrystallization-filtration (solvent: toluene/heptane=0.5/2 by volume) to give colorless crystals of 3-fluoro-4′-(4-propylcyclohexyl)biphenyl-4-ol (7.0 g, GC purity: 95%).

후처리

  1. temperaturethe mixture was heated
  2. extractionwas extracted with diethyl ether
  3. washThe extract was washed with water three times
  4. distillationthe solvent was distilled off
  5. customThe residue was purified by silica gel-column chromatography (solvent: toluene/ethyl acetate=10/1 by volume)
  6. filtrationby recrystallization-filtration (solvent: toluene/heptane=0.5/2 by volume)

출처 및 근거

ORD 기록
ord-b94ad96e1ee6426fba0f01c98761210c
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08609207B2

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