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

HRID 448448노트

반응식

HRID 448448 반응식
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]

참가 물질

7

반응물 4

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

생성물 1

HCID 583071913'-Ethoxy-4'-Methoxybiphenyl-3-Carboxylic Acid수율 76%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 80711,2-Dimethoxyethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-b775f6c250fb4a8d8703bc841047ada8
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08481568B2

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