Hydrochloric Acid → 4-Bromo-4'-methoxybenzophenone

HRID 229125

Reaction equation

HRID 229125 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[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:10]=[CH:9][C:5]([C:6]([C:14]2[CH:15]=[CH:16][C:11]([O:17][CH3:18])=[CH:12][CH:13]=2)=[O:7])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7519AnisoleHCID 685154-Bromobenzoyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 7943334-Bromo-4'-methoxybenzophenoneYield 100.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled (ice bath, 5° C.) mixture of 4-bromobenzoyl chloride (25.0 g, 0.114 mol) and anisole (15.5 g, 0.143 mol, 1.25 eq) in CH2Cl2 (500 mL) was added AlCl3 (19.0 g, 0.143 mol, 1.25 eq) portion-wise over a period of 20 minutes with stirring under a nitrogen atmosphere. The resulting reaction mixture was allowed to stir between 5° C. and 20° C. for 3 h. The reaction mixture was poured slowly into 20% aqueous HCl (500 mL), stirred for 15 min, and layers were separated. The aqueous layer was further extracted with CH2Cl2 (3×250 mL). The combined organic layer was washed with water (200 mL), brine (200 mL) dried (Na2SO4), filtered, and concentrated under reduced pressure to afford 33.48 g (100%) of compound 1 as a white solid. 1H NMR (300 MHz, CDCl3): δ 3.91 (s, 3H), 6.99 (d, J=8.7 Hz, 2H), 7.65 (s, 4H), 7.82 (d, J=8.7 Hz, 2H).

Workup

  1. temperatureTo a cooled
  2. customThe resulting reaction mixture
  3. stirringto stir between 5° C. and 20° C. for 3 h
  4. stirringstirred for 15 min
  5. customlayers were separated
  6. extractionThe aqueous layer was further extracted with CH2Cl2 (3×250 mL)
  7. washThe combined organic layer was washed with water (200 mL), brine (200 mL)
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b5dd5c6d5383494cb8c90b2123ce6d94
Source dataset
uspto-grants-2009_07
Patent number
US07560589B2

Linked notes

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