Allyl bromide → 3-Allyloxy-4-chloro-benzotrifluoride

HRID 2115907Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2115907
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[OH:12].C(=O)([O-])[O-].[K+].[K+].[CH2:19](Br)[CH:20]=[CH2:21]>CN(C)C=O.O>[CH2:21]([O:12][C:3]1[CH:4]=[C:5]([C:8]([F:10])([F:11])[F:9])[CH:6]=[CH:7][C:2]=1[Cl:1])[CH:20]=[CH2:19]

Komponenten

6

Edukt 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 123498Phenol, 2-chloro-5-(trifluoromethyl)-

Produkt 1

HCID 689686303-Allyloxy-4-chloro-benzotrifluoride

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 2-chloro-5-trifluoromethyl-phenol (10.00 g, 0.05 mol) in N,N-dimethylformamide (500 mL) was added potassium carbonate (28.12 g, 0.209 mol) followed by allyl bromide (7.38 g, 0.061 mol) and the reaction was allowed to stir at room temperature for 12 h. The reaction mixture was diluted with water (500 mL) to dissolve any solids and extracted with ethyl acetate (3×250 mL). The combined organic layers were washed with water (4×500 mL), saturated aqueous sodium chloride (400 mL), dried (magnesium sulfate) and the solvent removed in vacuo to give 2-(allyloxy)-1-chloro-4-(trifluoromethyl)benzene as a colorless oil. The oil was re-dissolved in mesitylene (35 mL) and heated at reflux for 12 h. Removal of the solvent in vacuo provided a crude oil. Purification by flash column chromatography (silica, ethyl acetate:hexanes 2:8) provided 9.6 g (96%) of 2-allyl-6-chloro-3-(trifluoromethyl)phenol as a amber oil. Rf=0.66 (silica, ethyl acetate:hexanes 1:4); 1H NMR (DMSO-d6) δH 9.84 (s, 1H); 7.43 (d, 2H); 7.16 (d, 1H); 5.84 (m, 1H); 4.95 (d, 1H); 4.89 (d, 1H); 3.46 (d, 2H).

Aufarbeitung

  1. dissolutionto dissolve any solids
  2. extractionextracted with ethyl acetate (3×250 mL)
  3. washThe combined organic layers were washed with water (4×500 mL), saturated aqueous sodium chloride (400 mL)
  4. dry with materialdried (magnesium sulfate)
  5. customthe solvent removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-361a5c84b3764210b845869b64a62c4b
Quelldatensatz
uspto-grants-2008_10
Patentnummer
US07435837B2

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