4'-Fluoroacetophenone → 1-(4-Fluorophenyl)-2-(3-methoxyphenyl)ethanone

HRID 595361

反応式

HRID 595361 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5](Cl)[CH:6]=[CH:7][CH:8]=1.[F:10][C:11]1[CH:16]=[CH:15][C:14]([C:17](=[O:19])[CH3:18])=[CH:13][CH:12]=1.P>C1(C)C=CC=CC=1.C(Cl)C=CC1C=CC=CC=1.[Pd]>[F:10][C:11]1[CH:16]=[CH:15][C:14]([C:17](=[O:19])[CH2:18][C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=2)=[CH:13][CH:12]=1

参加物

6

反応物 3

HCID 98284'-FluoroacetophenoneHCID 178333-ChloroanisoleHCID 24404Phosphine

生成物 1

HCID 431599671-(4-Fluorophenyl)-2-(3-methoxyphenyl)ethanone収率 75.9%

試薬・触媒・溶媒 2

HCID 131734589Palladium cinnamyl chloride触媒HCID 1140Toluene溶媒

実験手順

This reaction is carried out in the same manner as the reaction in example 3. The difference is that, the reactants are m-methoxyphenyl chloride (143.7 mg, 1.0 mmol), 1-(4′-fluorophenyl)ethanone (347.2 mg, 2.5 mmol), palladium cinnamyl chloride (7.8 mg, 0.015 mmol), 2-Methoxy-6-(N-methyl-N-phenyl-amino)phenyldicyclohexyl)phosphine (18.4 mg, 0.045 mmol), K3PO43H2O (664.2 mg, 2.5 mmol) in 3 mL dry toluene at 110° C. for 22.8 h. 1-(4′-Fluorophenyl)-2-(3′-methoxyphenyl)-1-ethanone (185.5 mg) was obtained with a yield of 75% as liquid. 1H NMR (300 MHz, CDCl3) δ 8.05-7.98 (m, 2H, ArH), 7.27-7.18 (m, 1H, ArH), 7.12-7.04 (m, 2H, ArH), 6.86-6.75 (m, 3H, ArH), 4.20 (s, 2H, CH2), 3.75 (s, 3H, OCH3); 13C NMR (75 MHz, CDCl3) δ 195.8, 167.2, 163.9, 159.7, 135.7, 132.8, 132.7, 131.2, 131.1, 129.6, 121.6, 115.7, 115.4, 115.0, 112.2, 55.0, 45.4; 19F NMR (282 MHz, CDCl3) 6-104.9; IR (neat) v (cm−1) 3072, 3002, 2940, 2836, 1682, 1597, 1506, 1491, 1455, 1437, 1331, 1264, 1232, 1157, 1099, 1050, 1002; MS (70 eV, EI) m/z (%): 245 (M++1, 3.27), 244 (M+, 17.36), 123 (100).

後処理

  1. customThis reaction is carried out in the same manner as the reaction in example 3
  2. customat 110° C.
  3. customfor 22.8 h

出典と根拠

ORDレコード
ord-2aa43d2537bc4039aec4286acb71312c
出典データセット
uspto-grants-2016_01
特許番号
US09243011B2

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