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

HRID 1030455Notes

Reaction equation

HRID 1030455 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:17])[CH3:16])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:18]Br>C(Cl)(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C:15](=[O:17])[CH2:16][Br:18])=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

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

Product 1

HCID 105425931-[4-(Benzyloxy)phenyl]-2-bromoethan-1-oneYield 34.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

4'-Benzyloxyacetophenone (55.0 g) was stirred in chloroform (500 ml), and bromine (13.0 ml) was added dropwise thereto at room temperature in 30 minutes. The mixture was stirred for 10 minutes, and the reaction mixture was washed with aqueous solution of sodium sulfate, water and saturated saline in turn, dried with anhydrous sodium sulfate and then concentrated. The precipitating crystals were recrystallized from acetone-diisopropyl ether to give 4'-benzyloxy-2-bromoacetophenone (25.7 g, 34.6%). m.p. 81°-82° C.

Workup

  1. washthe reaction mixture was washed with aqueous solution of sodium sulfate, water and saturated saline in turn
  2. dry with materialdried with anhydrous sodium sulfate
  3. concentrationconcentrated
  4. customThe precipitating crystals were recrystallized from acetone-diisopropyl ether

Sources & evidence

ORD record
ord-7ec635d9889d49d381fad0b6dd0ada0c
Source dataset
uspto-grants-1992_04
Patent number
US05106732

Reaction notes

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