4-Bromoanisole → (5-Bromo-2-methoxy-phenyl)-(2-chloro-4-nitro-phenyl)-methanone

HRID 2067217Notes

Reaction equation

HRID 2067217 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.[Cl:10][C:11]1[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[CH:17]=[CH:16][C:12]=1[C:13](Cl)=[O:14].[O-]S(C(F)(F)F)(=O)=O.[Bi+3].[O-]S(C(F)(F)F)(=O)=O.[O-]S(C(F)(F)F)(=O)=O>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[C:4]([C:13]([C:12]2[CH:16]=[CH:17][C:18]([N+:20]([O-:22])=[O:21])=[CH:19][C:11]=2[Cl:10])=[O:14])[CH:3]=1

Participants

5

Reactant 3

HCID 77304-BromoanisoleHCID 81522Benzoyl chloride, 2-chloro-4-nitro-HCID 9917655Bi(OTf)3

Product 1

HCID 68418361(5-Bromo-2-methoxy-phenyl)-(2-chloro-4-nitro-phenyl)-methanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-bromo-4-methoxy-benzene (7.48 g, 40 mmol), 2-chloro-4-nitro-benzoyl chloride (8.79 g, 40 mmol) and bismuth triflate (1.31 g, 2.0 mmol) under an atmosphere of argon was stirred at RT for 20 min. The temperature was raised to 80° C. and stirring was continued for 90 min. DCM was added to the reaction mixture and the organic phase was washed with aq. HCl (1 N, 0.5 mL) and NaHCO3 (aq.). The organic phase was dried (MgSO4), filtered and concentrated in vacuo to give the crude product. The crude product was crystallised from a mixture of DCM and pentane to afford the title compound as yellow crystals

Workup

  1. temperatureThe temperature was raised to 80° C.
  2. stirringstirring
  3. waitwas continued for 90 min
  4. washthe organic phase was washed with aq. HCl (1 N, 0.5 mL) and NaHCO3 (aq.)
  5. dry with materialThe organic phase was dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give the crude product
  9. customThe crude product was crystallised from a mixture of DCM and pentane

Sources & evidence

ORD record
ord-10fd4c9398ae4cdc9684ea6a25ee5266
Source dataset
uspto-grants-2012_10
Patent number
US08293772B2

Reaction notes

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