Anisole → 2-(3-Bromo-2,5-dimethoxy-phenyl)-1-(4-methoxy-phenyl)-ethanone

HRID 1794495Notes

Reaction equation

HRID 1794495 reaction equation
[Br:1][C:2]1[C:3]([O:14][CH3:15])=[C:4]([CH2:10][C:11]([OH:13])=O)[CH:5]=[C:6]([O:8][CH3:9])[CH:7]=1.O=S(Cl)Cl.[C:20]1([O:26][CH3:27])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[Al+3].[Cl-].[Cl-].[Cl-]>C(Cl)Cl.CO.CN(C=O)C>[Br:1][C:2]1[C:3]([O:14][CH3:15])=[C:4]([CH2:10][C:11]([C:23]2[CH:24]=[CH:25][C:20]([O:26][CH3:27])=[CH:21][CH:22]=2)=[O:13])[CH:5]=[C:6]([O:8][CH3:9])[CH:7]=1

Participants

8

Reactant 4

HCID 7519AnisoleHCID 24386Thionyl ChlorideHCID 6451240Aluminum(III) ChlorideHCID 10125382(3-Bromo-2,5-dimethoxy-phenyl)-acetic acid

Product 1

HCID 101502862-(3-Bromo-2,5-dimethoxy-phenyl)-1-(4-methoxy-phenyl)-ethanoneYield 75%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a cooled (0° C.) solution of 55 (2.8 g, 10 mmol) in CH2Cl2 (50 ml) was added SOCl2 (1.8 g, 15 mmol) and DMF (2 ml) and the reaction was stirred for 3 hr. The solution was concentrated and the resulting oil was taken up into dichloroethane (50 ml). The solution was cooled and anisole (2.0 g, 1 8.4 mmol) was added followed by AlCl3 (1.8 g, 13.8 mmol). The reaction was stirred for 1 hr and was then quenched with 2N HCl aq. The organic layer was dried over MgSO4, concentrated to give an oil which was taken up into MeOH and a solid crystallized. The solid was collected by filtration to give a white solid (2.3 g, 63%); Mp=91–93° C.; 1H NMR (DMSO-d6) δ 8.01 (d, 2 H, J=8.4 Hz), 7.10–7.05 (m, 3 H), 6.85 (d, 1 H, J=5.7 Hz), 4.35 (s, 2 H), 3.85 (s, 3 H), 3.72 (s, 3H), 3.59 (s, 3 H); MS 363/365 (M−H)−

Workup

  1. concentrationThe solution was concentrated
  2. temperatureThe solution was cooled
  3. stirringThe reaction was stirred for 1 hr
  4. customwas then quenched with 2N HCl aq. The organic layer
  5. dry with materialwas dried over MgSO4
  6. concentrationconcentrated
  7. customto give an oil which
  8. customa solid crystallized
  9. filtrationThe solid was collected by filtration

Sources & evidence

ORD record
ord-53c5d2a13ff6451093524eaae94520cc
Source dataset
uspto-grants-2006_04
Patent number
US07022733B2

Reaction notes

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