Hydrogen Bromide → 2-Bromo-4-(4-trifluoromethylphenyl)-1-indanone

HRID 1595247

Reaktionsgleichung

Reaktionsgleichung von HRID 1595247
[F:1][C:2]([F:20])([F:19])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:17]=[CH:16][CH:15]=[C:14]3[C:10]=2[CH2:11][CH2:12][C:13]3=[O:18])=[CH:5][CH:4]=1.[BrH:21].BrBr.S(=O)(O)[O-].[Na+]>C(O)(=O)C.ClCCl.O>[Br:21][CH:12]1[CH2:11][C:10]2[C:14](=[CH:15][CH:16]=[CH:17][C:9]=2[C:6]2[CH:5]=[CH:4][C:3]([C:2]([F:19])([F:20])[F:1])=[CH:8][CH:7]=2)[C:13]1=[O:18]

Komponenten

8

Edukt 4

HCID 260Hydrogen BromideHCID 24408BromineHCID 217020674-(4-Trifluoromethylphenyl)-1-indanoneHCID 23665763Sodium Bisulfite

Produkt 1

HCID 217020632-Bromo-4-(4-trifluoromethylphenyl)-1-indanone

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidLösungsmittel3×HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

2.76 g (10 mmol) of 4-(4-trifluoromethylphenyl)-1-indanone are dissolved in 20 ml of glacial acetic acid and, after addition of 10 μl of a 48% strength solution of HBr in glacial acetic acid, while stirring a solution of 0.516 ml (10.05 mmol) of bromine in glacial acetic acid is added. After 3 h at room temperature, the reaction mixture is poured into a mixture of 100 ml of water with 100 g of ice and 100 mg of sodium bisulfite, and the resulting suspension is shaken with dichloromethane. The organic phase is washed 3× with water, dried over sodium sulfate, filtered and concentrated in vacuo. The residue is chromatographed on silica gel with dichloromethane/n-heptane 3/1. 2-Bromo-4-(4-trifluoromethylphenyl)-1-indanone is obtained with a melting point of 102-105° C., in addition to a little 2,2-dibromo compound.

Aufarbeitung

  1. additionis added
  2. washThe organic phase is washed 3× with water
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue is chromatographed on silica gel with dichloromethane/n-heptane 3/1

Quellen und Nachweise

ORD-Eintrag
ord-148bb9a15717416e8eb685da85a7081b
Quelldatensatz
uspto-grants-2001_09
Patentnummer
US06288094B1

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