Hydrogen Bromide → 4-Bromobenzophenone

HRID 496300Notes

Reaction equation

HRID 496300 reaction equation
[BrH:1].N[C:3]1[CH:16]=[CH:15][C:6]([C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[O:8])=[CH:5][CH:4]=1.C([O-])([O-])=O.[K+].[K+]>CS(C)=O.CCOCC>[Br:1][C:3]1[CH:16]=[CH:15][C:6]([C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[O:8])=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 260Hydrogen BromideHCID 11430Potassium CarbonateHCID 143464-Aminobenzophenone

Product 1

HCID 70304-Bromobenzophenone

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 3283Diethyl EtherSolvent

Conditions

Temperature
35 °C

Procedure

A solution of 48% aqueous HBr (2.31 ml, 20 mmol) dissolved in DMSO (25 ml) was added dropwise to a solution of 4-aminobenzophenone (0.986 g, 5 mmol) in a mixture of 25 ml of DMSO and KNO2 (0.851 g, 10 mmol) at 35° C. with agitation. The added mixture was stirred at 35° C. for 10 minutes, and then transferred to a solution containing K2CO3 (5 g) in 100 ml ice-water. The reaction mixture was then taken up in ether, and then the ethereal extracts were washed with water and dried over anhydrous magnesium sulfate. Removal of the solvent under reduced pressure gave the crude 4-bromobenzophenone. The crude product was further purified by column chromatography to obtain 4-bromobenzophenone. The yield determined by gas chromatography was 72% (based on decane as an internal standard).

Workup

  1. washthe ethereal extracts were washed with water
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customRemoval of the solvent under reduced pressure
  4. customgave the crude 4-bromobenzophenone
  5. customThe crude product was further purified by column chromatography

Sources & evidence

ORD record
ord-4fff520db8a940169ad1aee659822a32
Source dataset
uspto-grants-2005_09
Patent number
US06943257B2

Reaction notes

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