Cesium carbonate → 4-(4-Bromo-2,5-dichlorophenoxy)nicotinic acid

HRID 1967006

반응식

HRID 1967006 반응식
Cl[C:2]1[C:7]([C:8]([OH:10])=[O:9])=[CH:6][N:5]=[CH:4][CH:3]=1.[Br:11][C:12]1[C:17]([Cl:18])=[CH:16][C:15]([OH:19])=[C:14]([Cl:20])[CH:13]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CC1C=CC=CC=1C>[Br:11][C:12]1[C:17]([Cl:18])=[CH:16][C:15]([O:19][C:2]2[C:7]([C:8]([OH:10])=[O:9])=[CH:6][N:5]=[CH:4][CH:3]=2)=[C:14]([Cl:20])[CH:13]=1

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 160224-Bromo-2,5-dichlorophenolHCID 8182294-Chloronicotinic acid

생성물 1

HCID 673204804-(4-Bromo-2,5-dichlorophenoxy)nicotinic acid

시약·촉매·용매 1

HCID 7237O-Xylene용매

반응 조건

온도
120 °C

실험 절차

To a stirred suspension of 6.0 g (38.08 mmol) 4-chloronicotinic acid (commercially available; CAS RN 10177-29-4) in 200 mL o-xylene were added 10.13 g (41.89 mmol) 4-bromo-2,5-dichlorophenol (commercially available; CAS RN 1940-42-7) and 2.84 g (7.62 mmol) tetrakis-(acetonitrile)-copper hexafluorophosphate (commercially available; CAS RN 64443-05-6). Then 31.31 g (95.20 mmol) cesium carbonate were added and the resulting dark brown suspension as heated to 120° C. for 16 hours. After cooling to room temperature, the solvent was evaporated, the residue dissolved in 1.25 l water, extracted four times with 250 mL ethyl acetate and filtered. The pH of the green filtrate was adjusted to 6 using 25% aqueous hydrochloric acid. The formed precipitate was filtered off to give a first batch of the desired compound. The pH of the filtrate was adjusted to pH 3 using 25% aqueous hydrochloric acid, the suspension stirred for 0.25 hours at room temperature and then kept in the fridge for 64 hours. The suspension was filtered and washed with water to yield another batch of compound. Brown solid (overall yield 5.63 g (41%)). MS (ESI): m/z=363.9 [M+H]+.

후처리

  1. temperatureAfter cooling to room temperature
  2. customthe solvent was evaporated
  3. dissolutionthe residue dissolved in 1.25 l water
  4. extractionextracted four times with 250 mL ethyl acetate
  5. filtrationfiltered
  6. filtrationThe formed precipitate was filtered off

출처 및 근거

ORD 기록
ord-8d8a55d382d74c9c8aa186d6fc881736
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08420647B2

연결된 노트

불러오는 중…