Chlorobenzene → 2-Phenyl-1-(p-tolyl)-1-propanone

HRID 595351

반응식

HRID 595351 반응식
[C:1]1(Cl)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:18])[CH2:16][CH3:17])=[CH:11][CH:10]=1.C(O[Na])(C)(C)C>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.COC1C=CC=C(N(C)C2C=CC=CC=2)C=1P(C1CCCCC1)C1CCCCC1>[C:1]1([CH:16]([CH3:17])[C:15]([C:12]2[CH:13]=[CH:14][C:9]([CH3:8])=[CH:10][CH:11]=2)=[O:18])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

참가 물질

7

반응물 3

HCID 7964ChlorobenzeneHCID 21429p-MethylpropiophenoneHCID 178418730sodium 2-methylpropan-2-olate

생성물 1

HCID 130960712-Phenyl-1-(p-tolyl)-1-propanone수율 97.5%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 71725627(2-Dicyclohexylphosphino-3-methoxy-N-methyl-N-phenylbenzenamine촉매HCID 1140Toluene용매

실험 절차

This reaction is carried out in the same manner as the reaction in example 3. The difference is that, the reactants are phenyl chloride (111.0 mg, 0.99 mmol), 1-(4-methylphenyl)-1-propanone (177.8 mg, 1.2 mmol), palladium acetate (6.7 mg, 0.030 mmol), 2-Methoxy-6-(N-methyl-N-phenyl-amino)phenyl(dicyclohexyl)phosphine (18.4 mg, 0.045 mmol), t-BuONa (115.8 mg, 1.2 mmol) in 3 mL dry toluene at 110° C. for 16.5 h. 2-Phenyl-1-(p-tolyl)-1-propanone (216.5 mg, contaminated with 11.9% of 1-(4-methylphenyl)propanone determined by 1H NMR) was obtained with a yield of 90% as liquid. 1H NMR (300 MHz, CDCl3) δ 7.87-7.80 (m, 2H, ArH), 7.30-7.20 (m, 4H, ArH), 7.20-7.08 (m, 3H, ArH), 4.64 (q, J=7.0 Hz, 1H, CH), 2.27 (s, 3H, ArCH3), 1.50 (d, J=7.0 Hz, 3H, CH3); 13C NMR (75 MHz, CDCl3) δ 199.7, 143.3, 141.6, 133.7, 129.0, 128.74, 128.72, 127.5, 126.6, 47.5, 21.3, 19.3; IR (neat) v (cm−1) 3061, 3028, 2975, 2930, 2870, 1682, 1606, 1570, 1492, 1452, 1408, 1372, 1332, 1304, 1253, 1225, 1210, 1177, 1008; MS (70 eV, EI) m/z (%): 224 (M+, 0.64), 119 (100).

후처리

  1. customThis reaction is carried out in the same manner as the reaction in example 3
  2. customat 110° C.
  3. customfor 16.5 h

출처 및 근거

ORD 기록
ord-a9186bd6383b46a3a59d5ca6a7f0c230
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09243011B2

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