Hydrogen Bromide → HCID 15460158, compound

HRID 2269297Notes

Reaction equation

HRID 2269297 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[C:10]3[C:14](=[CH:15][CH:16]=2)[C:13](=[O:17])[CH2:12][CH2:11]3)[CH:5]=[CH:6][CH:7]=1.[BrH:18].[Br:19]Br.OS([O-])=O.[Na+]>C(O)(=O)C.O>[Br:18][CH:12]1[CH2:11][C:10]2[C:14](=[CH:15][CH:16]=[C:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=3)[CH:9]=2)[C:13]1=[O:17].[Br:18][C:12]1([Br:19])[CH2:11][C:10]2[C:14](=[CH:15][CH:16]=[C:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=3)[CH:9]=2)[C:13]1=[O:17]

Participants

8

Reactant 4

HCID 260Hydrogen BromideHCID 24408BromineHCID 11333990HCID 11333990, compoundHCID 23665763Sodium Bisulfite

Product 2

HCID 15460158HCID 15460158, compoundHCID 18347156HCID 18347156, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 962WaterSolvent2×

Procedure

2.42 g (10 mmol) of 5-(3-chlorophenyl)indan-1-one are dissolved in 30 ml of glacial acetic acid and, after addition of 10 μof a 48% strength HBr solution in water, treated dropwise while stirring with a solution of 0.77 ml (15 mmol) of bromine in 7 ml of glacial acetic acid. After the reaction mixture has been stirred at room temperature for 3 h, it is poured into a mixture of 100 g of ice with 70 ml of water and 100 mg of NaHSO3 and stirred. The resulting suspension is extracted by shaking with 200 ml of dichloromethane, and the organic phase is then washed with water (3×100 ml), dried over magnesium sulfate, concentrated in vacuo and purified by chromatography on silica gel with toluene/ethyl acetate 50/1. 2-Bromo-5-(3-chlorophenyl)indan-1-one is obtained with a melting point of 110° C., in addition to a little 2,2-dibromo-5-(3-chlorophenyl)indan-1-one.

Workup

  1. additiontreated dropwise
  2. stirringstirred
  3. extractionThe resulting suspension is extracted
  4. stirringby shaking with 200 ml of dichloromethane
  5. washthe organic phase is then washed with water (3×100 ml)
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. custompurified by chromatography on silica gel with toluene/ethyl acetate 50/1

Sources & evidence

ORD record
ord-e37fe6eac3d64fad89a236ac73e841bb
Source dataset
uspto-grants-2001_12
Patent number
US06329407B1

Reaction notes

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