Hydrogen Bromide → HCID 15433015, compound

HRID 2288772Notes

Reaction equation

HRID 2288772 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]1[CH:4]=[C:5]([C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[C:14](=[O:18])[CH2:13][CH2:12]3)[CH:6]=[CH:7][CH:8]=1.[BrH:21].BrBr.C(=O)([O-])O.[Na+]>C(O)(=O)C.O>[Br:21][CH:13]1[CH2:12][C:11]2[C:15](=[CH:16][CH:17]=[C:9]([C:5]3[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:19])([F:20])[F:1])[CH:4]=3)[CH:10]=2)[C:14]1=[O:18]

Participants

7

Reactant 4

HCID 260Hydrogen BromideHCID 24408BromineHCID 516892Sodium BicarbonateHCID 11277377HCID 11277377, compound

Product 1

HCID 15433015HCID 15433015, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 962WaterSolvent2×

Procedure

1.79 g of 5-(3-trifluoromethylphenyl)indan-1-one are dissolved in 10 ml of glacial acetic acid. 5.5 μl of a 48% strength solution of hydrobromic acid in water are added and a solution of 0.362 ml of bromine in 5 ml of glacial acetic acid is then slowly added dropwise. The reaction mixture is stirred at room temperature for 3 hours and then poured into a mixture of 50 ml of water with 50 g of ice and 86 mg of sodium hydrogencarbonate. The aqueous suspension is extracted by shaking with 100 ml of dichloromethane, the organic phase is washed three times with 50 ml of water, dried over magnesium sulfate and concentrated, and the residue is chromatographed on silica gel using toluene/ethyl acetate 25/1. 2-Bromo-5-(3-trifluoromethylphenyl)indan-1-one of melting point 96° C. is obtained. 2,2-Dibromo-5-(3-trifluoromethylphenyl)indan-1-one of melting point 210° C. (dec.) is isolated as a by-product.

Workup

  1. extractionThe aqueous suspension is extracted
  2. stirringby shaking with 100 ml of dichloromethane
  3. washthe organic phase is washed three times with 50 ml of water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customthe residue is chromatographed on silica gel

Sources & evidence

ORD record
ord-b3ad5eeb3bc3494bbff9d2138bb2eb06
Source dataset
uspto-grants-2000_07
Patent number
US06090833

Reaction notes

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