Hydrochloric Acid → (3-bromophenyl)(4-methoxyphenyl)methanone

HRID 1525220Notes

Reaction equation

HRID 1525220 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5](Cl)=[O:6].[C:11]1([O:17][CH3:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[Al+3].[Cl-].[Cl-].[Cl-].Cl>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([C:5]([C:14]2[CH:15]=[CH:16][C:11]([O:17][CH3:18])=[CH:12][CH:13]=2)=[O:6])[CH:8]=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7519AnisoleHCID 74377Benzoyl chloride, 3-bromo-HCID 6451240Aluminum(III) Chloride

Product 1

HCID 2757031(3-bromophenyl)(4-methoxyphenyl)methanoneYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled (0° C.) mixture of 3-bromobenzoyl chloride (5-a, 178 g, 0.82 mol) and anisole (110 g, 1.03 mol) in DCM (2.0 L) was added AlCl3 (138 g, 1.03 mol) portion wise with stirring under N2. The resulting reaction mixture was allowed to stir at r.t overnight. The reaction mixture was poured into 20% HCl (1500 ml), stirred for 1 h, and layers were separated. The aqueous layer was further extracted with DCM (2×750 ml). The combined organic layer was washed with water, brine, dried (Na2SO4), filtered and concentrated under reduced pressure. The residue was washed with hexane to afford the product, 5-b, (190 g, 84%).

Workup

  1. temperatureTo a cooled
  2. customThe resulting reaction mixture
  3. stirringto stir at r.t overnight
  4. stirringstirred for 1 h
  5. customlayers were separated
  6. extractionThe aqueous layer was further extracted with DCM (2×750 ml)
  7. washThe combined organic layer was washed with water, brine
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. washThe residue was washed with hexane

Sources & evidence

ORD record
ord-ee54a0242dd64f06816a71100d74139b
Source dataset
uspto-grants-2015_07
Patent number
US09079930B2

Reaction notes

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