1-(2-Phenylpyrimidin-5-yl)ethanone → 2-Bromo-1-(2-phenylpyrimidin-5-yl)ethanone

HRID 42288

Reaktionsgleichung

Reaktionsgleichung von HRID 42288
[C:1]1([C:7]2[N:12]=[CH:11][C:10]([C:13](=[O:15])[CH3:14])=[CH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br-:16].[Br-].[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC>ClCCl>[Br:16][CH2:14][C:13]([C:10]1[CH:9]=[N:8][C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[N:12][CH:11]=1)=[O:15]

Komponenten

4

Edukt 2

HCID 226310721-(2-Phenylpyrimidin-5-yl)ethanoneHCID 23500184Tetra-n-butylammonium tribromide

Produkt 1

HCID 592524542-Bromo-1-(2-phenylpyrimidin-5-yl)ethanoneAusbeute 79,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

To a solution consisting of 1-(2-phenylpyrimidin-5-yl)ethanone (Step A, 700 mg, 3.5 mmol) in dichloromethane (25 mL) was added tetrabutylammonium tribromide (1.87 g, 3.90 mmol). The reaction mixture was sealed with a screw top and warmed at 40° C. for 5 hours and allowed to cool to room temperature over a weekend. The pale yellow precipitate formed was collected on a filter and washed with 1:1 dichloromethane-hexane to afford the title intermediate (770 mg, 79%); Rf 0.31 with 9:1 v/v hexanes-ethyl acetate; MS (ESI+) m/z 279, 277 (M+1, Br isotopes).

Aufarbeitung

  1. customThe reaction mixture was sealed with a screw top
  2. temperatureto cool to room temperature over a weekend
  3. customThe pale yellow precipitate formed
  4. customwas collected on
  5. filtrationa filter
  6. washwashed with 1:1 dichloromethane-hexane

Quellen und Nachweise

ORD-Eintrag
ord-49ef573663a4412a8513614681ec736e
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08536185B2

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