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

HRID 273401

反応式

HRID 273401 の反応式
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

参加物

9

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 178418397HCID 178418397、化合物触媒HCID 702Ethanol溶媒HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
90 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-cbe6b4fbe9b945ec9dd0c15d5272c25b
出典データセット
uspto-grants-2008_11
特許番号
US07456218B2

関連ノート

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