Aluminum(III) Chloride → Methyl 4-(2-(5-bromo-2-hydroxy-4-methoxyphenyl)-2-oxoethyl)benzoate

HRID 1184972Notes

Reaction equation

HRID 1184972 reaction equation
[Br:1][C:2]1[C:3]([O:23][CH3:24])=[CH:4][C:5]([O:21]C)=[C:6]([C:8](=[O:20])[CH2:9][C:10]2[CH:19]=[CH:18][C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][CH:11]=2)[CH:7]=1.[Al+3].[Cl-].[Cl-].[Cl-]>C(Cl)Cl>[Br:1][C:2]1[C:3]([O:23][CH3:24])=[CH:4][C:5]([OH:21])=[C:6]([C:8](=[O:20])[CH2:9][C:10]2[CH:11]=[CH:12][C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:18][CH:19]=2)[CH:7]=1

Participants

4

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 67366966HCID 67366966, compound

Product 1

HCID 67368371Methyl 4-(2-(5-bromo-2-hydroxy-4-methoxyphenyl)-2-oxoethyl)benzoateYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 4-(2-(5-bromo-2,4-dimethoxyphenyl)-2-oxoethyl)benzoate (1.1 g, 2.8 mmol) in DCM (100 mL) was added AlCl3 (7.4 g, 56 mmol) and the mixture was stirred at room temperature for 1 h. Then the mixture was poured into ice-water (100 mL), extracted with DCM (20 mL×4). The organic phase was washed with brine (30 mL), dried with Na2SO4, filtered and the filtrate was concentrated in vacuo to give brown oil, which was purified by prep-TLC (PE/EA=3/1) to afford Intermediate J (750 mg, 71%) as a light yellow solid. MS (ESI): m/z 379.0 [M+1]+.

Workup

  1. extractionextracted with DCM (20 mL×4)
  2. washThe organic phase was washed with brine (30 mL)
  3. dry with materialdried with Na2SO4
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated in vacuo
  6. customto give brown oil, which
  7. customwas purified by prep-TLC (PE/EA=3/1)

Sources & evidence

ORD record
ord-69bb68514c664070a2fa1274027da494
Source dataset
uspto-grants-2014_03
Patent number
US08669381B2

Reaction notes

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