Sulfuric Acid → 3-Bromo-5-formylbenzoic acid

HRID 1845338Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1845338
[CH:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([OH:8])=[O:7])=[O:2].S(=O)(=O)(O)O.[Br:17]N1C(=O)CCC1=O>>[Br:17][C:10]1[CH:9]=[C:5]([CH:4]=[C:3]([CH:1]=[O:2])[CH:11]=1)[C:6]([OH:8])=[O:7]

Komponenten

4

Edukt 3

HCID 1118Sulfuric AcidHCID 120773-CarboxybenzaldehydeHCID 67184N-bromobutanimide

Produkt 1

HCID 223207963-Bromo-5-formylbenzoic acidAusbeute 85,1 %

Versuchsvorschrift

Into a round bottom flask were combined 3-formylbenzoic acid (10.0 g, 66.6 mmol) and sulfuric acid (653 g, 6.66 mol). N-Bromosuccinimide (14.23 g, 79.9 mmol) was added portion wise over a 10 minute period and the reaction was stirred at room temperature for 3 h upon which the mixture was poured over ice. The white precipitate that formed was filtered, washed with cold water (5×100 mL), and recrystallized from water-ethanol to afford the title compound as a white solid (12.98 g, 76.6%). LC-MS: 227.0 [M−1]−; 1H NMR (400 MHz, DMSO-d6): 10.05 (s, 1H), 8.40 (t, 1H, J=1.5 Hz), 8.3 (d, 2H, J=1.5 Hz).

Aufarbeitung

  1. customInto a round bottom flask were combined
  2. additionwas poured over ice
  3. customThe white precipitate that formed
  4. filtrationwas filtered
  5. washwashed with cold water (5×100 mL)
  6. customrecrystallized from water-ethanol

Quellen und Nachweise

ORD-Eintrag
ord-783ce336ab2949c2912e3de7e460977c
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08946439B2

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