Acetonitrile → 3-chloro-4-[(4-chlorobenzyl)oxy]benzaldehyde

HRID 253382Notes

Reaction equation

HRID 253382 reaction equation
C(#N)C.[Cl:4][C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][C:12]=1[OH:13])[CH:8]=[O:9].[Cl:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19]Br)=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+]>O>[Cl:4][C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][C:12]=1[O:13][CH2:19][C:18]1[CH:21]=[CH:22][C:15]([Cl:14])=[CH:16][CH:17]=1)[CH:8]=[O:9]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 170223-Chloro-4-hydroxybenzaldehydeHCID 693291-(Bromomethyl)-4-chlorobenzene

Product 1

HCID 8187873-chloro-4-[(4-chlorobenzyl)oxy]benzaldehyde

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

To acetonitrile (15.0 mL) were added 3-chloro-4-hydroxy-benzaldehyde (29, 0.6 g, 4 mmol), 4-chlorobenzyl bromide (22, 1.2 g, 6 mmol), and potassium carbonate (0.9 g, 7 mmol). The reaction was heated to 150° C. for 10 minutes in a CEM Discover microwave instrument. The reaction was poured into water, extracted with ethyl acetate, and washed with brine. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated. The desired compound was isolated by silica gel column chromatography (ethyl acetate:hexanes) (31, 0.85 g, 76%).

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with brine
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ab03a12356da42859bb4da56e0705a98
Source dataset
uspto-grants-2011_01
Patent number
US07872018B2

Reaction notes

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