Acetophenone → 2-(3-Methoxyphenyl)-1-phenylethan-1-one

HRID 595359

Reaction equation

HRID 595359 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5](Cl)[CH:6]=[CH:7][CH:8]=1.[C:10]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)(=[O:12])[CH3:11].P>C1(C)C=CC=CC=1.C(Cl)C=CC1C=CC=CC=1.[Pd]>[O:2]([C:3]1[CH:4]=[C:5]([CH2:11][C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:12])[CH:6]=[CH:7][CH:8]=1)[CH3:1]

Participants

6

Reactant 3

HCID 7410AcetophenoneHCID 178333-ChloroanisoleHCID 24404Phosphine

Product 1

HCID 27596142-(3-Methoxyphenyl)-1-phenylethan-1-oneYield 84%

Reagents, catalysts & solvents 2

HCID 131734589Palladium cinnamyl chlorideCatalystHCID 1140TolueneSolvent

Procedure

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 (142.7 mg, 1.0 mmol), acetophenone (299.9 mg, 2.5 mmol), palladium cinnamyl chloride (7.8 mg, 0.015 mmol), 2-Methoxy-6-(N-methyl-N-phenyl-amino)phenyldicyclohexyl)phosphine (18.3 mg, 0.045 mmol), K3PO43H2O (663.9 mg, 2.5 mmol) in 3 mL dry toluene at 110° C. for 12 h. 2-(3′-Methoxylphenyl)-1-phenyl-1-ethanone (189.0 mg) was obtained with a yield of 84% as liquids. 1H NMR (300 MHz, CDCl3) δ 8.02-7.96 (m, 2H, ArH), 7.55-7.47 (m, 1H, ArH), 7.46-7.38 (m, 2H, ArH), 7.21 (t, J=7.8 Hz, 1H, ArH), 6.87-6.73 (m, 3H, ArH), 4.22 (s, 2H, CH2), 3.73 (s, 3H, OCH3); 13C NMR (75 MHz, CDCl3) δ 197.3, 159.6, 136.3, 135.9, 133.0, 129.5, 128.47, 128.45, 121.6, 115.0, 112.2, 55.0, 45.4; IR (neat) v (cm−1) 3058, 3002, 2938, 2835, 1682, 1597, 1490, 1448, 1317, 1263, 1211, 1153, 1050, 1020, 1001; MS (70 eV, EI) m/z (%): 227 (M++1, 2.28), 226 (M+, 12.78), 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 12 h

Sources & evidence

ORD record
ord-788d17177a904d67be013d5d125f8c89
Source dataset
uspto-grants-2016_01
Patent number
US09243011B2

Linked notes

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