Potassium Carbonate → Methyl 2'-methyl-2-nitro-1,1'-biphenyl-4-carboxylate

HRID 219776

反応式

HRID 219776 の反応式
Br[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].[C:15]1([CH3:24])[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1B(O)O.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.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>[CH3:24][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13]

参加物

7

反応物 3

HCID 11430Potassium CarbonateHCID 27332672-Methylphenyl boronic acidHCID 2736829Methyl 4-bromo-3-nitrobenzoate

生成物 1

HCID 59606541Methyl 2'-methyl-2-nitro-1,1'-biphenyl-4-carboxylate収率 79.9%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 1140Toluene溶媒

反応条件

温度
120 °C

実験手順

To a solution of methyl 4-bromo-3-nitrobenzoate (Chess, 3 g, 11.53 mmol) in toluene (100 mL) and water (100 mL) was added o-tolylboronic acid (1.88 g, 13.84 mmol) followed by potassium carbonate (7.972 g, 57.68 mmol), tetrakis(triphenylphosphine)palladium(0) (0.668 g, 0.577 mmol). The reaction mixture was refluxed at 120° C. for 14 h. After the completion of reaction, it was cooled to RT and organic layer was separated and evaporated under reduced pressure. The crude compound was passed through silica pad (60-120 mesh) using hexane as eluent to give the title compound as a white solid (2.5 g, 79%). 1H NMR: (DMSO-d6, 400 MHz) δ 8.52 (s, 1H), 8.29-8.26 (m, 1H), 7.63-7.61 (m, 1H), 7.34-7.33 (m, 2H), 7.23 (m, 1H), 7.13 (m, 1H), 3.94 (s, 3H), 2.04 (s, 3H).

後処理

  1. customAfter the completion of reaction, it
  2. temperaturewas cooled to RT
  3. customorganic layer was separated
  4. customevaporated under reduced pressure

出典と根拠

ORDレコード
ord-41538cc7baf64588a9bc20fb5653d958
出典データセット
uspto-grants-2012_06
特許番号
US08202865B2

関連ノート

読み込み中…