Hydrochloric Acid → 3',4'-Dimethoxy-2-bromoisobutyrophenone

HRID 2395723Notes

Reaction equation

HRID 2395723 reaction equation
[C:1]1([O:9][CH3:10])[C:2](=[CH:5][CH:6]=[CH:7][CH:8]=1)[O:3][CH3:4].[Br:11][C:12]([CH3:17])([CH3:16])[C:13](Br)=[O:14].[Cl-].[Al+3].[Cl-].[Cl-].Cl>>[CH3:4][O:3][C:2]1[CH:5]=[C:6]([C:13](=[O:14])[C:12]([Br:11])([CH3:17])[CH3:16])[CH:7]=[CH:8][C:1]=1[O:9][CH3:10]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 7043VeratroleHCID 886852-Bromo-2-methylpropionyl bromideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 132202043',4'-Dimethoxy-2-bromoisobutyrophenoneYield 42.9%

Procedure

A mixture of veratrole (1,3-dimethoxybenzene) (13.8 g), 2-bromoisobutyryl bromide (23.0 g) and aluminium chloride (14.0 g) was heated for 1 hour at 70°-80° C. After cooling, ice and hydrochloric acid were added to the reaction mixture which was then extracted with ether. The extract was washed first with water and then with 1N NaOH-solution, dried and the solvent evaporated in vacuo, yielding a pale yellow oil (12.3 g).

Workup

  1. temperaturewas heated for 1 hour at 70°-80° C
  2. temperatureAfter cooling
  3. extractionwas then extracted with ether
  4. washThe extract was washed first with water
  5. dry with materialwith 1N NaOH-solution, dried
  6. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-f865642f8bca47b38438ad07d91af23e
Source dataset
uspto-grants-1996_02
Patent number
US05489614

Reaction notes

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