Sulfuric Acid → 3-Bromo-5-formylbenzoic acid

反応式

[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]

参加物

反応物 3

HCID 1118Sulfuric Acid

HCID 120773-Carboxybenzaldehyde

HCID 67184N-bromobutanimide

生成物 1

HCID 223207963-Bromo-5-formylbenzoic acid収率 85.1%

実験手順

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).