1-Phenyl-1-propanone → 1-Phenyl-2-(m-tolyl)-1-propanone

HRID 595349Notes

Reaction equation

HRID 595349 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5](Cl)=[CH:4][CH:3]=1.[C:9]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)(=[O:12])[CH2:10][CH3:11].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:13]1([C:9](=[O:12])[CH:10]([C:4]2[CH:3]=[C:2]([CH3:1])[CH:7]=[CH:6][CH:5]=2)[CH3:11])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

7

Reactant 3

HCID 71481-Phenyl-1-propanoneHCID 78104-ChlorotolueneHCID 178418730sodium 2-methylpropan-2-olate

Product 1

HCID 153028111-Phenyl-2-(m-tolyl)-1-propanoneYield 85%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 71725627(2-Dicyclohexylphosphino-3-methoxy-N-methyl-N-phenylbenzenamineCatalystHCID 1140TolueneSolvent

Procedure

This reaction is carried out in the same manner as the reaction in example 3. The difference is that, the reactants are p-methyphenyl chloride (126.6 mg, 1.0 mmol), propiophenone (161.1 mg, 1.2 mmol), palladium acetate (6.6 mg, 0.029 mmol), 2-Methoxy-6-(N-methyl-N-phenyl-amino)phenyl(dicyclohexyl)phosphine (18.4 mg, 0.045 mmol), t-BuONa (115.4 mg, 1.2 mmol) in 3 mL dry toluene at 110° C. for 16.5 h. 1-Phenyl-2-(m-tolyl)-1-propanone (190.0 mg) was obtained with a yield of 85% as liquid. 1H NMR (300 MHz, CDCl3) δ 8.10-7.94 (m, 2H, ArH), 7.52-7.44 (m, 1H, ArH), 7.44-7.35 (m, 2H, ArH), 7.25-7.18 (m, 1H, ArH), 7.17-7.10 (m, 2H, ArH), 7.07-7.02 (m, 1H, ArH), 4.69 (q, J=6.8 Hz, 1H, CH), 2.33 (s, 3H, ArCH3), 1.57 (d, J=6.8 Hz, 3H, CH3); 13C NMR (75 MHz, CDCl3) δ 200.2, 141.3, 138.5, 136.4, 132.6, 128.73, 128.66, 128.3, 128.2, 127.6, 124.8, 47.7, 21.3, 19.4; IR (neat) v (cm−1) 3058, 3025, 2975, 2930, 2870, 1682, 1605, 1596, 1583, 1488, 1448, 1372, 1338, 1238, 1208, 1181, 1158, 1075, 1002; MS (70 eV, EI) m/z (%): 224 (M+, 4.20), 105 (100).

Workup

  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

Sources & evidence

ORD record
ord-41cb3aee72e04806863c82b578aa9b02
Source dataset
uspto-grants-2016_01
Patent number
US09243011B2

Reaction notes

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