Hydrochloric Acid → (3,5-Dibromo-4-methylphenyl)methanol

HRID 1667508Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1667508
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([Br:13])[C:11]=1[CH3:12])[C:5](OC)=[O:6].[BH4-].[Na+].Cl>C(O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH2:5][OH:6])[CH:9]=[C:10]([Br:13])[C:11]=1[CH3:12]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 624016Methyl 3,5-dibromo-4-methylbenzoateHCID 4311764Sodium borohydride

Produkt 1

HCID 60156325(3,5-Dibromo-4-methylphenyl)methanolAusbeute 72,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of methyl 3,5-dibromo-4-methylbenzoate (15 g, 48.706 mmol), NaBH4 (5.53 g, 146.18 mmol) and absolute ethanol (175 mL) was heated to reflux for 4 h. The mixture was cooled, followed by acidification with 2N HCl. The solids were filtered through celite and rinsed with EtOAc. The filtrate was poured onto water and extracted. The organic layer was washed with brine and dried (Na2SO4). Chromatography (Hexanes/EtOAc) afforded (3,5-dibromo-4-methyl-phenyl)-methanol (9.94 g) as a white solid. 1H NMR (400 MHz, d6-DMSO) δ: 2.48 (s, 3H), 4.45 (d, 2H), 5.38 (t, 1H), 7.57 (s, 2H) ppm.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux for 4 h
  3. temperatureThe mixture was cooled
  4. filtrationThe solids were filtered through celite
  5. washrinsed with EtOAc
  6. additionThe filtrate was poured onto water
  7. extractionextracted
  8. washThe organic layer was washed with brine
  9. dry with materialdried (Na2SO4)

Quellen und Nachweise

ORD-Eintrag
ord-4f30819e3f114251b81fcbc8592ced18
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08044041B2

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