4-Methyl-3-(trifluoromethyl)benzoic acid → 4-(Bromomethyl)-3-(trifluoromethyl)benzoic acid

HRID 1184845Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1184845
[Br:1]([O-])(=O)=O.[Na+].[CH3:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[CH:9][C:8]=1[C:16]([F:19])([F:18])[F:17].S(=O)(O)[O-].[Na+]>O.C(OCC)(=O)C.CCOCC>[Br:1][CH2:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[CH:9][C:8]=1[C:16]([F:17])([F:18])[F:19]

Komponenten

7

Edukt 3

HCID 27755924-Methyl-3-(trifluoromethyl)benzoic acidHCID 23665763Sodium BisulfiteHCID 23668195Sodium Bromate

Produkt 1

HCID 231458934-(Bromomethyl)-3-(trifluoromethyl)benzoic acidAusbeute 81,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittel2×HCID 3283Diethyl EtherLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a solution of sodium bromate (1109 mg, 7.35 mmol) in H2O (3.3 mL) was added 4-methyl-3-trifluoromethyl-benzoic acid (500 mg, 2.449 mmol) in ethyl acetate (5 mL), followed by a solution of sodium bisulfite (765 mg, 7.35 mmol) in H2O (9 mL) over a period of about 15 min. The mixture was stirred overnight at room temperature and overnight at 50° C. The mixture was poured in ether (50 mL). The aqueous layer was extracted twice with ether and the combined organic layer was washed with anhydrous Na2S2O3 solution, dried, filtered and concentrated in vacuo to give the crude 4-(bromomethyl)-3-(trifluoromethyl)benzoic acid 35 (563 mg, 81%) which was used without further purification. (m/z)=282 and 284 (M+H)+.

Aufarbeitung

  1. extractionThe aqueous layer was extracted twice with ether
  2. washthe combined organic layer was washed with anhydrous Na2S2O3 solution
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-17e57dc3f99f4701b61acd8c4b8203f1
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08669256B2

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