Hydrogen Bromide → 2-Bromo-4'-methylacetophenone

HRID 273485Notes

Reaction equation

HRID 273485 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:10])=[O:9])=[CH:4][CH:3]=1.[BrH:11].BrBr.O>C(O)(=O)C>[Br:11][CH2:10][C:8]([C:5]1[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=1)=[O:9]

Participants

6

Reactant 4

HCID 260Hydrogen BromideHCID 962WaterHCID 8500p-METHYLACETOPHENONEHCID 24408Bromine

Product 1

HCID 692722-Bromo-4'-methylacetophenoneYield 65%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Conditions

Temperature
30 °C

Procedure

To a stirring solution of 20 g (150 mmol) of 4-methylacetophenone in 100 mL of glacial acetic acid was added catalytic amount of HBr (0.5 mL) followed by 21.40 g (134 mmol) of bromine dissolved in acetic acid (30 mL) dropwise at 10-15° C. The reaction mixture was stirred at 25-35° C. for 5 hrs, then poured into water (100 mL). The solid that separated was filtered to give the required product (20 g, 65%).

Workup

  1. customThe solid that separated
  2. filtrationwas filtered

Sources & evidence

ORD record
ord-f250061689bf4f54a12f10513c567adc
Source dataset
uspto-grants-2008_11
Patent number
US07456288B2

Reaction notes

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