3-Nitrophenylboronic Acid → Methyl 3-(3-nitrophenyl)benzoate

HRID 1053600

反応式

HRID 1053600 の反応式
C(=O)([O-])[O-].[Na+].[Na+].Br[C:8]1[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:10][C:9]=1[C:18](OC)=O.[N+:22]([C:25]1[CH:26]=C(B(O)O)[CH:28]=[CH:29][CH:30]=1)([O-:24])=[O:23].ClCCl>O1CCOCC1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[N+:22]([C:25]1[CH:26]=[C:18]([C:9]2[CH:8]=[CH:17][CH:16]=[C:11]([C:12]([O:14][CH3:15])=[O:13])[CH:10]=2)[CH:28]=[CH:29][CH:30]=1)([O-:24])=[O:23]

参加物

7

反応物 4

HCID 16773-Nitrophenylboronic AcidHCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 2824912Dimethyl 4-bromoisophthalate

生成物 1

HCID 11708671Methyl 3-(3-nitrophenyl)benzoate収率 151.8%

試薬・触媒・溶媒 2

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
85 °C

実験手順

Tetrakis(triphenylphosphine) palladium(0) (1.04 g, 0.90 mmol, 0.03 equiv.) and sodium carbonate (4.8 g, 45.28 mmol, 1.52 eqiuv.) were added to a stirred mixture of dimethyl 4-bromoisophthalate (1.26 g, 4.61 mmol) and 3-nitrophenylboronic acid (5.16 g, 30.91 mmol, 0.03 eqiuv.) in 1,4-dioxane (50 mL). The mixture was stirred at about 85° C. for about 16 hours, and then was cooled to ambient temperature. Standard extractive workup with dichloromethane (3×100 mL) gave a crude residue was then purified by silica gel column chromatography (ethyl acetate/petroleum ether) to afford the title product as a white solid (1.8 g; yield=23%). 1H NMR (300 MHz, CDCl3) δ: 8.52 (s, 1H), 8.33 (s, 1H), 8.26 (d, J=2.4 Hz, 1H), 8.14 (d, J=2.7 Hz, 1H), 7.99 (d, J=1.8 Hz, 1H), 7.86 (d, J=2.1 Hz, 1H), 7.67 (m, 2H), 4.00 (s, 3H).

後処理

  1. temperaturewas cooled to ambient temperature
  2. customwas then purified by silica gel column chromatography (ethyl acetate/petroleum ether)

出典と根拠

ORDレコード
ord-e09d05bd78a14f398a3402416244a230
出典データセット
uspto-grants-2016_07
特許番号
US09394239B2

関連ノート

読み込み中…