Réaction #531806

Équation de réaction

Benzyl bromide

2-Bromo-5-hydroxy-4-methoxybenzaldehyde

K2CO3

acetonitrile

→

2

Rendement 83.0%

5-Benzyloxy-2-bromo-4-methoxybenzaldehyde

Rendement 83.0%

Solvants

water

Conditions de réaction

Traitement

1. 1
   Autreflushed with Ar
2. 2
   TempératureAfter cooling
3. 3
   Extractionextracted with CH2Cl2 (300 mL)
4. 4
   LavageThe CH2Cl2 was washed with water (3×100 mL)
5. 5
   Autredried
6. 6
   Concentrationconcentrated
7. 7
   AutreRecrystallization with isopropanol: water (3:1)

Mode opératoire

2-Bromo-5-hydroxy-4-methoxybenzaldehyde (25 g, 0.108 mol) and K2CO3 (30 g, 0.216 mol) were added to acetonitrile (250 mL) and flushed with Ar. Benzyl bromide (20 g, 0.12 mol) was added and the mixture was heated under Ar for 20 h at 50° C. After cooling, the mixture was poured into water (200 ml) and extracted with CH2Cl2 (300 mL). The CH2Cl2 was washed with water (3×100 mL), dried and concentrated. Recrystallization with isopropanol: water (3:1) gave 28.8 g (83%) of 2 as a light brown solid. 1H-NMR (400 MHz, CDCl3) dH 3.96 (3H, s, OCH3), 5.16 (2H, s, CH2Ph), 7.07-7.48 (7H, m, ArH+CH2Ph), 10.16 (1H, s, CHO).

Source