Water → 3'-Ethoxy-4'-Methoxybiphenyl-3-Carboxylic Acid

HRID 448448ノート

反応式

HRID 448448 の反応式
Br[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4]N=1.[CH2:11]([O:13][C:14]1[CH:15]=[C:16](B(O)O)[CH:17]=[CH:18][C:19]=1[O:20][CH3:21])[CH3:12].[C:25]([O-])([O-])=O.[Na+].[Na+].O>COCCOC.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>[CH2:11]([O:13][C:14]1[CH:15]=[C:16]([C:25]2[CH:2]=[CH:10][CH:9]=[C:5]([C:6]([OH:8])=[O:7])[CH:4]=2)[CH:17]=[CH:18][C:19]=1[O:20][CH3:21])[CH3:12]

参加物

7

反応物 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 2389326-Bromonicotinic acidHCID 46738762(3-Ethoxy-4-methoxyphenyl)boronic acid

生成物 1

HCID 583071913'-Ethoxy-4'-Methoxybiphenyl-3-Carboxylic Acid収率 76%

試薬・触媒・溶媒 2

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

実験手順

6-Bromonicotinic acid (2.02 g, 10.0 mmol) was dissolved in DME (80 mL) under nitrogen. Pd(PPh3)4 (0.58 g, 0.5 mmol) was added, and the resulting mixture was stirred at ambient temperature for 15 minutes. 3-ethoxy-4-methoxyphenylboronic acid (2.4 g, 12.2 mmol) and 2N Na2CO3 (40 mL, 80 mmol) were added, and the resulting mixture was heated to reflux with stirring for 24 hours. The mixture was poured into 300 mL of water and extracted with ethyl acetate (3×200 mL), and the product precipitated upon standing, providing 2.05 g of the product in 76% yield: 1H NMR (CDCl3) δ 1.53 (t, J=7.0 Hz, 3H), 3.96 (s, 3H), 4.22 (q, J=7.0 Hz, 2H), 7.00 (d, J=8.6 Hz, 1H), 7.53-7.58 (m, 2H), 7.91-8.02 (m, 2H), 8.12 (dd, J=6.9 Hz, J=1.5 Hz, 1H).

後処理

  1. temperaturethe resulting mixture was heated
  2. temperatureto reflux
  3. stirringwith stirring for 24 hours
  4. extractionextracted with ethyl acetate (3×200 mL)
  5. customthe product precipitated

出典と根拠

ORDレコード
ord-b775f6c250fb4a8d8703bc841047ada8
出典データセット
uspto-grants-2013_07
特許番号
US08481568B2

反応ノート

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