Potassium Carbonate → Methyl 4-nitro-2-vinylbenzoate

HRID 514274ノート

反応式

HRID 514274 の反応式
Br[C:2]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].C(=O)([O-])[O-].[K+].[K+].[CH:21](B1OB(C=C)OB(C=C)O1)=[CH2:22]>COCCOC.O.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>[N+:12]([C:10]1[CH:9]=[CH:8][C:3]([C:4]([O:6][CH3:7])=[O:5])=[C:2]([CH:21]=[CH2:22])[CH:11]=1)([O-:14])=[O:13]

参加物

7

反応物 3

HCID 11430Potassium CarbonateHCID 2734807TrivinylboroxinHCID 15833211Methyl 2-Bromo-4-nitrobenzoate

生成物 1

HCID 57663378Methyl 4-nitro-2-vinylbenzoate収率 47.1%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒2 回HCID 80711,2-Dimethoxyethane溶媒

実験手順

12.0 g (46.1 mmol) of methyl 2-bromo-4-nitrobenzoate were initially charged in 240 ml of 1,2-dimethoxyethane, 2.66 g (2.30 mmol) of tetrakis(triphenylphosphine)palladium were added, and the mixture was stirred for 20 min. Subsequently, a solution of 6.38 g (46.1 mmol) of potassium carbonate in 80 ml of water and 11.11 g (46.1 mmol) of 2,4,6-trivinylcyclotriboroxane were added. The reaction mixture was stirred at reflux temperature for 20 hours. After cooling, the mixture was added to water and extracted with ethyl acetate, the organic phases were dried with magnesium sulphate, and the solvent was distilled off under reduced pressure. The residue was chromatographed using silica gel with cyclohexane/ethyl acetate (ratio 6:1) as the eluent. 4.5 g (46% of theory) of methyl 4-nitro-2-vinylbenzoate were obtained.

後処理

  1. stirringThe reaction mixture was stirred
  2. temperatureat reflux temperature for 20 hours
  3. temperatureAfter cooling
  4. extractionextracted with ethyl acetate
  5. dry with materialthe organic phases were dried with magnesium sulphate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe residue was chromatographed

出典と根拠

ORDレコード
ord-aaa347896b754c61a5b2f5e6c69cc3e9
出典データセット
uspto-grants-2015_08
特許番号
US09107411B2

反応ノート

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