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

HRID 585581ノート

反応式

HRID 585581 の反応式
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

参加物

8

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 178418397HCID 178418397、化合物触媒HCID 702Ethanol溶媒HCID 1140Toluene溶媒HCID 57417360Sodium chloride; water溶媒

反応条件

温度
95 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-5e9422330af34dbcacaf82cbaef32e18
出典データセット
uspto-grants-2005_08
特許番号
US06933321B2

反応ノート

読み込み中…