4-Chlorobenzophenone → 1-(4'-Benzoylphenyl)-2-propanone

HRID 595367

反応式

HRID 595367 の反応式
[C:1]([C:9]1[CH:14]=[CH:13][C:12](Cl)=[CH:11][CH:10]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P>CC(C)=O.C(Cl)C=CC1C=CC=CC=1.[Pd]>[C:1]([C:9]1[CH:14]=[CH:13][C:12]([CH2:2][C:1](=[O:8])[CH3:9])=[CH:11][CH:10]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 2

HCID 86534-ChlorobenzophenoneHCID 24404Phosphine

生成物 1

HCID 111283451-(4'-Benzoylphenyl)-2-propanone収率 163.8%

試薬・触媒・溶媒 2

HCID 131734589Palladium cinnamyl chloride触媒HCID 180Acetone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 4-Benzoylphenyl chloride (216.3 mg, 1.0 mmol), palladium cinnamyl chloride (7.8 mg, 0.015 mmol), 2-Methoxy-6-(N-methyl-N-phenyl-amino) henyldicyclohexyl)phosphine (24.5 mg, 0.060 mmol), Cs2OC3 (651.5 mg, 2.0 mmol) in 4.0 mL acetone at 90° C. for 12 h. 1-(4′-Benzoylphenyl)-2-propanone (195.2 mg) was obtained with a yield of 82% as liquid. 1H NMR (300 MHz, CDCl3) δ 7.83-7.75 (m, 4H, ArH), 7.62-7.54 (m, 1H, ArH), 7.52-7.43 (m, 2H, ArH), 7.35-7.28 (m, 2H, ArH), 3.81 (s, 2H, CH2), 2.22 (s, 3H, CH3); 13C NMR (75 MHz, CDCl3) δ 205.1, 196.1, 138.8, 137.4, 136.1, 132.3, 130.3, 129.8, 129.3, 128.1, 50.5, 29.5; IR (neat) v (cm−1) 3059, 3003, 2917, 1715, 1660, 1651, 1606, 1579, 1447, 1416, 1358, 1317, 1278, 1227, 1178, 1159, 1113, 1075, 1020, 1001; MS (70 eV, EI) m/z (%): 239 (M++1, 0.98), 238 (M+, 5.45), 196 (100).

後処理

  1. customThis reaction is carried out in the same manner as the reaction in example 3
  2. customat 90° C.
  3. customfor 12 h

出典と根拠

ORDレコード
ord-9426187b4f624ef5bb1e900fe97bbdd9
出典データセット
uspto-grants-2016_01
特許番号
US09243011B2

関連ノート

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