Dichloromethane → 2-Amino-3-bromo-5-methylbenzaldehyde

HRID 854942Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 854942
[NH2:1][C:2]1[C:7]([Br:8])=[CH:6][C:5]([CH3:9])=[CH:4][C:3]=1[CH2:10][OH:11].ClCCl>O1CCCC1.[O-2].[O-2].[Mn+4]>[NH2:1][C:2]1[C:7]([Br:8])=[CH:6][C:5]([CH3:9])=[CH:4][C:3]=1[CH:10]=[O:11]

Komponenten

5

Edukt 2

HCID 6344DichloromethaneHCID 20351850(2-Amino-3-bromo-5-methylphenyl)methanol

Produkt 1

HCID 109768082-Amino-3-bromo-5-methylbenzaldehydeAusbeute 78,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418406HCID 178418406, VerbindungKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

The (2-amino-3-bromo-5-methylphenyl)methanol (7.80 g, 36.1 mmol) was dissolved in tetrahydrofuran (20 mL). Dichloromethane (50 mL) was added along with activated carbon (16.3 g). Manganese dioxide (9.4 g, 108 mmol) was added and the solution stirred at 40° C. for 16 h. The solution was cooled to room temperature and vacuum filtered through a celite. The solvent was removed at reduced pressure and the 2-amino-3-bromo-5-methylbenzaldehyde (6.10 g, 28.5 mmol) obtained by recrystallization from diethyl ether/hexanes (1:10, 100 mL) (78% yield): Melting point 99.6-101.2° C. 1H NMR (300 MHz, CDCL3) 9.77 (s, 1H), 7.46 (s, 1H), 7.26 (s, 1H), 6.48 (bs, 2H), 2.76 (s, 3H). HRMS m/z 213.9902; calcd for M+H 213.9962.

Aufarbeitung

  1. temperatureThe solution was cooled to room temperature
  2. filtrationvacuum filtered through a celite
  3. customThe solvent was removed at reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-d0aee0a4c00348dfb1298ef1942ee089
Quelldatensatz
uspto-grants-2007_08
Patentnummer
US07259266B2

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