Bromine → HCID 23365458, compound

HRID 1033424Notes

Reaction equation

HRID 1033424 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:14](=[O:16])[CH3:15])=[CH:4][CH:3]=1.[Br:17]Br.BrBr.C(O)(=O)C>C(O)(=O)C.CCCCCC>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:14](=[O:16])[CH2:15][Br:17])=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 24408Bromine3×HCID 98372111-(4'-Methyl[1,1'-biphenyl]-2-yl)ethanoneHCID 87433071bromine AcOH

Product 1

HCID 23365458HCID 23365458, compoundYield 943.7%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
30 °C

Procedure

A solution of 4'-methyl-2-acetyl-1,1'-biphenyl (2.06 g, 9.79 mmol) in 10 mL of glacial acetic acid was treated dropwise with a solution of bromine (1.722 g, 1.07 mmol) dissolved in 3.0 mL of glacial acetic acid. After initiating the reaction with the first few drops of the bromine/acetic acid reagent by heating the reaction mixture at 30° C., the remainder of the bromine solution was added dropwise at 25°-30° C. The reaction mixture was stirred at room temperature until the consumption of bromine was complete (approximately 2 hrs). The reaction mixture was diluted with 150 mL of hexane then washed with water (3×50 mL). The organic layer was removed, dried over magnesium sulfate, filtered and evaporated under vacuum to give 2.92 g of an oil that was used in the next step without purification. 1H NMR (crude product) (200 MHz,CDCl3): 2.38 (s,3H), 3.66 (s,2H), 7.21 (s,4 H), 7.3-7.6 (m,4H).

Workup

  1. custom(approximately 2 hrs)
  2. washthen washed with water (3×50 mL)
  3. customThe organic layer was removed
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated under vacuum

Sources & evidence

ORD record
ord-ddc401460c1047238c347d37f9256ba7
Source dataset
uspto-grants-1994_05
Patent number
US05310737

Reaction notes

Loading…