Reaction #531806

Reaction equation

Benzyl bromide

2-Bromo-5-hydroxy-4-methoxybenzaldehyde

K2CO3

acetonitrile

→

2

Yield 83.0%

5-Benzyloxy-2-bromo-4-methoxybenzaldehyde

Yield 83.0%

Solvents

water

Conditions

Workup

1. 1
   Otherflushed with Ar
2. 2
   TemperatureAfter cooling
3. 3
   Extractionextracted with CH2Cl2 (300 mL)
4. 4
   WashThe CH2Cl2 was washed with water (3×100 mL)
5. 5
   Otherdried
6. 6
   Concentrationconcentrated
7. 7
   OtherRecrystallization with isopropanol: water (3:1)

Procedure

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