Aluminum(III) Chloride → 1-(2-Bromo-5-hydroxy-4-methoxyphenyl)ethan-1-one

HRID 41942Notes

Reaction equation

HRID 41942 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([O:10]C(C)C)=[CH:4][C:3]=1[C:14](=[O:16])[CH3:15].[Al+3].[Cl-].[Cl-].[Cl-]>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([OH:10])=[CH:4][C:3]=1[C:14](=[O:16])[CH3:15]

Participants

4

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 667608062'-Bromo-5'-isopropoxy-4'-methoxyacetophenone

Product 1

HCID 349091311-(2-Bromo-5-hydroxy-4-methoxyphenyl)ethan-1-oneYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
18 °C

Procedure

A solution of ketone 38 (220 mg, 0.766 mmol) in dry CH2Cl2 (2.0 mL) was treated with AlCl3 (306 mg, 2.29 mmol) and the resulting mixture stirred at 18° C. under a nitrogen atmosphere for 2 h. The ensuing mixture was partitioned between H2O (5 mL) and CH2Cl2 (5 mL) then the separated aqueous phase extracted with CH2Cl2 (1×15 mL). The combined organic fractions were dried (MgSO4), filtered and concentrated under reduced pressure and the ensuing residue subjected to flash chromatography (15:85 v/v ethyl acetate/hexane elution) to afford the title compound 39 (184 mg, 98%) as a pale-yellow solid, m.p. 109.7-111.4° C., Rf 0.4 in 1:1 v/v ethyl acetate/hexane.

Workup

  1. customThe ensuing mixture was partitioned between H2O (5 mL) and CH2Cl2 (5 mL)
  2. extractionthe separated aqueous phase extracted with CH2Cl2 (1×15 mL)
  3. dry with materialThe combined organic fractions were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. washthe ensuing residue subjected to flash chromatography (15:85 v/v ethyl acetate/hexane elution)

Sources & evidence

ORD record
ord-cd01f9518abd4690b32111d9710e19ff
Source dataset
uspto-grants-2013_09
Patent number
US08536157B2

Reaction notes

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