2-Chloroanisole → 2-Methoxyphenylacetone

HRID 595365Notes

Reaction equation

HRID 595365 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1Cl.P>CC(C)=O.C(Cl)C=CC1C=CC=CC=1.[Pd]>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:4][C:3](=[O:2])[CH3:8]

Participants

5

Reactant 2

HCID 130112-ChloroanisoleHCID 24404Phosphine

Product 1

HCID 788872-MethoxyphenylacetoneYield 179.9%

Reagents, catalysts & solvents 2

HCID 131734589Palladium cinnamyl chlorideCatalystHCID 180AcetoneSolvent

Procedure

This reaction is carried out in the same manner as the reaction in example 3. The difference is that, the reactants are o-methoxyphenyl chloride (142.3 mg, 1.0 mmol), palladium cinnamyl chloride (7.9 mg, 0.015 mmol), 2-Methoxy-6-(N-methyl-N-phenyl-amino) henyldicyclohexyl)phosphine (24.5 mg, 0.060 mmol), CS2CO3 (653.0 mg, 2.0 mmol) in 4.0 mL acetone at 90° C. for 16 h. 1-(2′-Methoxyphenyl)-2-propanone (147.7 mg) was obtained with a yield of 89% as liquid. 1H NMR (300 MHz, CDCl3) δ 7.29-7.22 (m, 1H, ArH), 7.14-7.09 (m, 1H, ArH), 6.94-6.84 (m, 2H, ArH), 3.79 (s, 3H, OCH3), 3.66 (s, 2H, CH2), 2.12 (s, 3H, COCH3); 13C NMR (75 MHz, CDCl3) δ 206.9, 157.2, 131.0, 128.4, 123.5, 120.5, 110.3, 55.2, 45.4, 29.1; IR (neat) v (cm−1) 3003, 2941, 2905, 2837, 1713, 1602, 1589, 1496, 1464, 1439, 1356, 1322, 1290, 1247, 1176, 1160, 1115, 1050, 1030; MS (70 eV, EI) m/z (%): 165 (M++1, 6.45), 164 (M+, 50.19), 91 (100).

Workup

  1. customThis reaction is carried out in the same manner as the reaction in example 3
  2. customat 90° C.
  3. customfor 16 h

Sources & evidence

ORD record
ord-9c9b0ffaa08d4ff6bf2e73724e157a48
Source dataset
uspto-grants-2016_01
Patent number
US09243011B2

Reaction notes

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