Water → Methyl 3-[4-[(4'-chloro-2'-methylbiphenyl-3-yl)methoxy]phenyl]propanoate

HRID 273401

반응식

HRID 273401 반응식
Br[C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][CH:21]=1)[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][C:15]([O:17][CH3:18])=[O:16])=[CH:9][CH:8]=1.[Cl:22][C:23]1[CH:28]=[CH:27][C:26](B(O)O)=[C:25]([CH3:32])[CH:24]=1.C(=O)([O-])[O-].[Na+].[Na+].O>C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1(C)C=CC=CC=1.C(O)C>[Cl:22][C:23]1[CH:28]=[CH:27][C:26]([C:2]2[CH:21]=[CH:20][CH:19]=[C:4]([CH2:5][O:6][C:7]3[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][C:15]([O:17][CH3:18])=[O:16])=[CH:9][CH:8]=3)[CH:3]=2)=[C:25]([CH3:32])[CH:24]=1

참가 물질

9

반응물 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 5017600(4-Chloro-2-methylphenyl)boronic acidHCID 23136270Methyl 4-[(3-bromophenyl)methoxy]benzenepropanoate

생성물 1

HCID 58903150Methyl 3-[4-[(4'-chloro-2'-methylbiphenyl-3-yl)methoxy]phenyl]propanoate수율 88.5%

시약·촉매·용매 4

HCID 178418397HCID 178418397, 화합물촉매HCID 702Ethanol용매HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

반응 조건

온도
90 °C

실험 절차

A mixture of methyl 3-[4-[(3-bromobenzyl)oxy]phenyl]propanoate (0.5 g, 1.43 mmol), 4-chloro-2-methylphenylboronic acid (0.30 g, 1.72 mmol), tetrakis(triphenylphosphine)palladium(0) (0.083 g, 0.072 mmol), sodium carbonate (0.46 g, 4.29 mmol), water (5 mL), ethanol (5 mL) and toluene (25 mL) was stirred under an argon atmosphere at 90° C. for 16 hrs. The reaction mixture was cooled, diluted with ethyl acetate, washed with water and saturated brine, dried and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-4/1) to give the title compound (0.50 g, yield 88%) as a colorless oil.

후처리

  1. temperatureThe reaction mixture was cooled
  2. washwashed with water and saturated brine
  3. customdried
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-4/1)

출처 및 근거

ORD 기록
ord-cbe6b4fbe9b945ec9dd0c15d5272c25b
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07456218B2

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