Sodium borohydride → Methyl 3-bromo-5-(hydroxymethyl)-4-methylbenzoate

HRID 337658Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 337658
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([CH:13]=[O:14])[C:11]=1[CH3:12])[C:5]([O:7][CH3:8])=[O:6].[BH4-].[Na+]>CO>[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([CH2:13][OH:14])[C:11]=1[CH3:12])[C:5]([O:7][CH3:8])=[O:6]

Komponenten

4

Edukt 2

HCID 4311764Sodium borohydrideHCID 86651684Methyl 3-bromo-5-formyl-4-methylbenzoate

Produkt 1

HCID 66896191Methyl 3-bromo-5-(hydroxymethyl)-4-methylbenzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a methanol (0.1 M) solution of methyl 3-bromo-5-formyl-4-methylbenzoate (1 eq.) from the previous step was added sodium borohydride (4 eq.) portionwise. The resulting mixture was stirred at RT for 3 h. The reaction was subsequently quenched with cold 10% aq. HCl and extracted with ether. The combined organic extracts were then washed with water and brine, dried over Na2SO4 and filtered. Concentration of the filtrate in vacuo afforded the title compound as a white solid.

Aufarbeitung

  1. customThe reaction was subsequently quenched with cold 10% aq. HCl
  2. extractionextracted with ether
  3. washThe combined organic extracts were then washed with water and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-fafbeae335f44fd68172e70daf5e7c8a
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08889714B2

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