N-bromobutanimide → 2-(4-Bromomethyl-3-trifluoromethyl-phenyl)-propan-2-ol

HRID 1970190Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1970190
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([OH:11])([CH3:10])[CH3:9])=[CH:4][C:3]=1[C:12]([F:15])([F:14])[F:13].[Br:16]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:16][CH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([OH:11])([CH3:10])[CH3:9])=[CH:4][C:3]=1[C:12]([F:13])([F:14])[F:15]

Komponenten

5

Edukt 2

HCID 67184N-bromobutanimideHCID 672412752-(4-Methyl-3-trifluoromethyl-phenyl)-propan-2-ol

Produkt 1

HCID 672413992-(4-Bromomethyl-3-trifluoromethyl-phenyl)-propan-2-olAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 7187Benzoyl PeroxideKatalysatorHCID 5943Carbon TetrachlorideLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

A mixture of 2-(4-Methyl-3-trifluoromethyl-phenyl)-propan-2-ol (0.436 g, 2 mmol), N-Bromosuccinimide (356 mg, 2 mmol) and benzoyl peroxide (15 mg) in CCl4 (8 mL) was stirred at 85° C. for 16 hrs. The reaction mixture was then partitioned between saturated aqueous NaHCO3 and DCM. DCM layer was dried over Na2SO4, filtered, and the solvent evaporated in vacuo to yield a crude solid which was purified via flash chromatography (15% EtOAc in n-heptane) to yield the title compound as a solid (450 mg, 76%)

Aufarbeitung

  1. customThe reaction mixture was then partitioned between saturated aqueous NaHCO3 and DCM
  2. dry with materialDCM layer was dried over Na2SO4
  3. filtrationfiltered
  4. customthe solvent evaporated in vacuo
  5. customto yield a crude solid which
  6. customwas purified via flash chromatography (15% EtOAc in n-heptane)

Quellen und Nachweise

ORD-Eintrag
ord-e8ee87f661c146acb822e605fae1ca3e
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08426604B2

Notizen zur Reaktion

Wird geladen…