Phenetole → (5-Bromo-2-chlorophenyl)(4-ethoxyphenyl)methanone

HRID 1849980Notes

Reaction equation

HRID 1849980 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH3:2].[Al+3].[Cl-].[Cl-].[Cl-].[Br:14][C:15]1[CH:16]=[CH:17][C:18]([Cl:24])=[C:19]([CH:23]=1)[C:20](Cl)=[O:21]>C(Cl)Cl>[Br:14][C:15]1[CH:16]=[CH:17][C:18]([Cl:24])=[C:19]([C:20]([C:7]2[CH:8]=[CH:9][C:4]([O:3][CH2:1][CH3:2])=[CH:5][CH:6]=2)=[O:21])[CH:23]=1

Participants

5

Reactant 3

HCID 7674PhenetoleHCID 27568715-Bromo-2-chlorobenzoyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 10020105(5-Bromo-2-chlorophenyl)(4-ethoxyphenyl)methanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-2.5 °C

Procedure

At −5-0° C., ethoxybenzene (20.5 g) and AlCl3 (22.3 g) were added into a solution of 5-bromo-2-chlorobenzoyl chloride (from step 2) in dry DCM (200 mL). Then the mixture was stirred at −5-0° C. for 1 h. The mixture was poured into ice-H2O (200 mL) and extracted with DCM. The organic phase was washed with 1M HCl, H2O, IM NaOH and brine. And the organic phase was concentrated, and the crude was purified by silica-gel column chromatography (PE/EA=80/1-40/1), to obtain 30 g of (5-bromo-2-chloro phenyl)(4-ethoxyphenyl)methanone.

Workup

  1. extractionextracted with DCM
  2. washThe organic phase was washed with 1M HCl, H2O, IM NaOH and brine
  3. concentrationAnd the organic phase was concentrated
  4. customthe crude was purified by silica-gel column chromatography (PE/EA=80/1-40/1)

Sources & evidence

ORD record
ord-afeabf6766624b9fb8ba78993442d7f9
Source dataset
uspto-grants-2015_02
Patent number
US08957033B2

Reaction notes

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