Sodium Bicarbonate → 4'-Fluoro-2'-methoxy-3-trifluoromethyl-biphenyl-4-carbonitrile

HRID 585581노트

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HRID 585581 반응식
Br[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([C:10]([F:13])([F:12])[F:11])[CH:3]=1.C([O-])(O)=O.[Na+].[F:19][C:20]1[CH:25]=[CH:24][C:23](B(O)O)=[C:22]([O:29][CH3:30])[CH:21]=1>C1(C)C=CC=CC=1.CCO.[Cl-].[Na+].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>[F:19][C:20]1[CH:25]=[CH:24][C:23]([C:2]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([C:10]([F:13])([F:12])[F:11])[CH:3]=2)=[C:22]([O:29][CH3:30])[CH:21]=1

참가 물질

8

반응물 3

HCID 516892Sodium BicarbonateHCID 2782672(4-Fluoro-2-methoxyphenyl)boronic acidHCID 223378254-Bromo-2-(trifluoromethyl)benzonitrile

생성물 1

HCID 223378244'-Fluoro-2'-methoxy-3-trifluoromethyl-biphenyl-4-carbonitrile수율 81%

시약·촉매·용매 4

HCID 178418397HCID 178418397, 화합물촉매HCID 702Ethanol용매HCID 1140Toluene용매HCID 57417360Sodium chloride; water용매

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온도
95 °C

실험 절차

In a round bottom flask under argon, 4-bromo-2-trifluoromethylbenzonitrile (1 g, 4 mmol) was solubilized in a mixture of toluene (55 mL) and EtOH (20 mL). Aq. NaHCO3 (20 ml, 5 eq., 0.8 M solution) and 4-fluoro-2-methoxyphenylboronic acid (816 mg, 4.8 mmol) were added. The mixture was degassed under the stream of argon for 10 min. Then Pd(PPh3)4 (462 mg, 0.4 mmol) was added and the mixture was heated at 95° C. for 2 hr. After it was cooled, the mixture was poured in brine and extracted with CH2Cl2. This organic layer was dried (MgSO4), filtered and evaporated. Chromatography on a silica gel (250 ml, EtOAc:hexanes, 1:9), gave a white solid (951 mg, 81%), 1H NM (300 MHz, acetone-d6)δ: 8.02-8.14 (m, 3H, C2,5,6—H), 7.53 (dd, 1H, J=8, 7 Hz, C6′—H), 7.03 (dd, 1H, J=11, 2 Hz, C3′—H), 6.89 (td, 1H, J=8, 2Hz, C5′—H).

후처리

  1. customThe mixture was degassed under the stream of argon for 10 min
  2. temperatureAfter it was cooled
  3. extractionextracted with CH2Cl2
  4. dry with materialThis organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated

출처 및 근거

ORD 기록
ord-5e9422330af34dbcacaf82cbaef32e18
출처 데이터셋
uspto-grants-2005_08
특허 번호
US06933321B2

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