Bromine → 1-[4-(Benzyloxy)phenyl]-2-bromoethan-1-one

HRID 2107024Notes

Reaction equation

HRID 2107024 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:6][CH:5]=1)=[O:3].O1CCOCC1.[Br:24]Br>[Cl-].[Al+3].[Cl-].[Cl-].O1CCCC1>[Br:24][CH2:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:6][CH:5]=1)=[O:3]

Participants

6

Reactant 3

HCID 24408BromineHCID 312751,4-DioxaneHCID 2452261-[4-(Benzyloxy)phenyl]ethan-1-one

Product 1

HCID 105425931-[4-(Benzyloxy)phenyl]-2-bromoethan-1-oneYield 76%

Reagents, catalysts & solvents 2

HCID 6451240Aluminum(III) ChlorideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

After dissolving 4.0 g of 4-benzyloxyacetophenone into 20 ml of 1,4-dioxane and 20 ml of tetrahydrofuran, 0.1 g of anhydrous aluminum chloride and 3.1 g of bromine were added under ice cooling and stirring. Further, after stirring for 5 hours under ice cooling, the reaction solution was concentrated to solid. Water and chloroform were added to the residue to separate liquid layers. Then, the chloroform layer was dried over anhydrous sodium sulfate and then concentrated to solid followed by purification by silica gel column chromatography using benzene/n-hexane (1:1) as an elute, to obtain 4.1 g of 2-bromo-1-(4-benzyloxy-phenyl)-ethanone. Then, using 3.0 g of the thus obtained bromide, 2.2 g of (Z)-2-(4-methyl-piperazin-1-yl)-1-(4-benzyloxy-phenyl)-ethanone oxime hydrochloride with the melting point of from 208° to 210° C. (decomposition) and 0.7 g of (E)-2-(4-methyl-piperazin-1-yl)-1-(4-benzyloxy-phenyl)-ethanone oxime hydrochloride with the melting point of from 210° to 212° C. were obtained in the same manner as in Example 1.

Workup

  1. additionwere added under ice cooling
  2. stirringFurther, after stirring for 5 hours under ice cooling
  3. concentrationthe reaction solution was concentrated to solid
  4. additionWater and chloroform were added to the residue
  5. customto separate liquid layers
  6. dry with materialThen, the chloroform layer was dried over anhydrous sodium sulfate
  7. concentrationconcentrated to solid
  8. customfollowed by purification by silica gel column chromatography

Sources & evidence

ORD record
ord-087056b248074e4da14e31b697346f81
Source dataset
uspto-grants-1990_06
Patent number
US04933344

Reaction notes

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