Sodium Carbonate → 3-Fluoro-5-methoxy-[1,1'-biphenyl]-4-carbonitrile

HRID 922389ノート

反応式

HRID 922389 の反応式
Br[C:2]1[CH:9]=[C:8]([O:10][CH3:11])[C:5]([C:6]#[N:7])=[C:4]([F:12])[CH:3]=1.[C:13]1(B(O)O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.CCO.CCOC(C)=O>[F:12][C:4]1[CH:3]=[C:2]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:9]=[C:8]([O:10][CH3:11])[C:5]=1[C:6]#[N:7]

参加物

7

反応物 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 574422094-Bromo-2-fluoro-6-methoxybenzonitrile

生成物 1

HCID 867193543-Fluoro-5-methoxy-[1,1'-biphenyl]-4-carbonitrile収率 97.9%

試薬・触媒・溶媒 3

HCID 702Ethanol触媒HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

A mixture of 4-bromo-2-fluoro-6-methoxybenzonitrile (2, 5.22 g, 22.7 mmol), phenylboronic acid (4.15 g, 34 mmol) and 2 M Na2CO3 (23 mL) in toluene (100 mL) was purged with N2 for 10 min. Pd(PPh4)3 (2.62 g, 27.7 mmol) and EtOH (5 drops) were added. The mixture was then heated under N2 in a sealed tube at 80° C. for 18 h. The mixture was cooled to room temperature, diluted with EtOAc (300 mL), filtered through celite, concentrated and purified by silica gel chromatography eluting with ethyl acetate in hexane (0-100%) to afford the title compound (5.05 g, 97%) as a white solid: 1H NMR (500 MHz, CDCl3) δ 7.57-7.55 (m, 2H), 7.50-7.23 (m, 3H), 7.01-6.99 (m, 1H), 6.93 (s, 1H), 3.95 (s, 3H).

後処理

  1. customwas purged with N2 for 10 min
  2. temperatureThe mixture was cooled to room temperature
  3. filtrationfiltered through celite,
  4. concentrationconcentrated
  5. custompurified by silica gel chromatography
  6. washeluting with ethyl acetate in hexane (0-100%)

出典と根拠

ORDレコード
ord-45247b0850884ec0865cfe97db91ac0b
出典データセット
uspto-grants-2016_03
特許番号
US09278940B2

反応ノート

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