Phenethyl bromide → 3,5-Dichloro-2-phenethoxybenzaldehyde

HRID 430094Notes

Reaction equation

HRID 430094 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([Cl:10])[CH:7]=[C:4]([CH:5]=[O:6])[C:3]=1[OH:11].C([O-])([O-])=O.[K+].[K+].Br[CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CN(C=O)C.O>[Cl:1][C:2]1[C:3]([O:11][CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[C:4]([CH:7]=[C:8]([Cl:10])[CH:9]=1)[CH:5]=[O:6]

Participants

6

Reactant 3

HCID 7666Phenethyl bromideHCID 11430Potassium CarbonateHCID 666603,5-Dichlorosalicylaldehyde

Product 1

HCID 183536653,5-Dichloro-2-phenethoxybenzaldehydeYield 70%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To 3,5-dichlorosalicylaldehyde (229 mg, 1.2 mmol) in DMF (5 ml) was added K2CO3 (1.06 g, 7.7 mmol) followed by (2-bromoethyl)benzene (0.14 ml, 1.0 mmol). The mixture was stirred under argon for five days then diluted with H2O (30 ml), extracted with Et2O (3×50 ml), dried (MgSO4), filtered, and concentrated in vacuo to give the title compound as a white powder (207 mg, 0.7 mmol, 70%); δH (CDCl3) 3.17 (2H, t), 4.31 (2H, t), 7.19-7.36 (5H, m), 7.60 (1H, d), 7.67 (1H, d), 9.95 (1H, s).

Workup

  1. extractionextracted with Et2O (3×50 ml)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-146b3c04bb1d4e34b285963a497c4d91
Source dataset
uspto-grants-2001_11
Patent number
US06320051B1

Reaction notes

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