Hydrochloric Acid → 1-(3-(Difluoromethyl)phenyl)ethan-1-one

HRID 623547

反応式

HRID 623547 の反応式
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH:8]([F:10])[F:9])[CH:3]=1.C([Sn](CCCC)(CCCC)[C:16]([O:18]CC)=[CH2:17])CCC.Cl>C1(C)C=CC=CC=1.C(OCC)(=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>[F:9][CH:8]([F:10])[C:4]1[CH:3]=[C:2]([C:16](=[O:18])[CH3:17])[CH:7]=[CH:6][CH:5]=1

参加物

7

反応物 3

HCID 313Hydrochloric AcidHCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 27696751-Bromo-3-(difluoromethyl)benzene

生成物 1

HCID 675101191-(3-(Difluoromethyl)phenyl)ethan-1-one収率 98%

試薬・触媒・溶媒 3

HCID 178418476HCID 178418476、化合物触媒HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

A mixture of 1-bromo-3-(difluoromethyl)benzene (0.72 g, 3.48 mmol), tributyl(1-ethoxyvinyl)tin (1.38 g, 3.83 mmol), dichlorobis(triphenylphosphine)-palladium(II) (0.24 g, 0.35 mmol) in toluene (12 mL) is heated at 100° C. under nitrogen atmosphere for 16 hours. After cooling to room temperature, 2M hydrochloric acid (12 mL) is added to the mixture. Then the resulting mixture is stirred at room temperature for 1 hour. The mixture is diluted with ethyl acetate (100 mL) and washed with water (100 mL). The organic layer is dried over sodium sulfate, and concentrated under reduced pressure. The residue is purified by column chromatography on silica-gel eluting with n-hexane/ethyl acetate (30:1) to give 0.58 g (98% yield) of the title compound as colorless oil.

後処理

  1. temperatureAfter cooling to room temperature
  2. washwashed with water (100 mL)
  3. dry with materialThe organic layer is dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue is purified by column chromatography on silica-gel
  6. washeluting with n-hexane/ethyl acetate (30:1)

出典と根拠

ORDレコード
ord-7c6a5cf691324612944f048a01b81bdb
出典データセット
uspto-grants-2016_04
特許番号
US09302991B2

関連ノート

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