Acetonitrile → 5-(Benzyloxy)-2-bromo-4-methoxybenzaldehyde

HRID 444624Notes

Reaction equation

HRID 444624 reaction equation
[Br:1][C:2]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([OH:12])=[CH:6][C:3]=1[CH:4]=[O:5].C([O-])([O-])=O.[K+].[K+].C(#N)C.[CH2:22](Br)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>O>[CH2:22]([O:12][C:7]1[C:8]([O:10][CH3:11])=[CH:9][C:2]([Br:1])=[C:3]([CH:6]=1)[CH:4]=[O:5])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 6160682-Bromo-5-hydroxy-4-methoxybenzaldehyde

Product 1

HCID 109033195-(Benzyloxy)-2-bromo-4-methoxybenzaldehydeYield 83%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

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).

Workup

  1. customflushed with Ar
  2. temperatureAfter cooling
  3. extractionextracted with CH2Cl2 (300 mL)
  4. washThe CH2Cl2 was washed with water (3×100 mL)
  5. customdried
  6. concentrationconcentrated
  7. customRecrystallization with isopropanol: water (3:1)

Sources & evidence

ORD record
ord-dd77b5c646954f9197777bd4683773f4
Source dataset
uspto-grants-2013_07
Patent number
US08475776B2

Reaction notes

Loading…