1,3-Dibromopropane → 2-Benzyl-1-(3-bromo-propoxy)-4-chloro-benzene

HRID 2219206Notes

Reaction equation

HRID 2219206 reaction equation
C([O-])([O-])=O.[K+].[K+].[CH2:7]([C:14]1[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:15]=1[OH:21])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[Br:22][CH2:23][CH2:24][CH2:25]Br.CCOC(C)=O>CN(C=O)C.O>[CH2:7]([C:14]1[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:15]=1[O:21][CH2:25][CH2:24][CH2:23][Br:22])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

7

Reactant 4

HCID 80011,3-DibromopropaneHCID 8425ChloropheneHCID 8857Ethyl AcetateHCID 11430Potassium Carbonate

Product 1

HCID 692752372-Benzyl-1-(3-bromo-propoxy)-4-chloro-benzeneYield 72.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Powdered K2CO3 (2.07 g, 15.0 mmol) is added to a stirred solution of 2-benzyl-4-chlorophenol (2.19 g, 10.0 mmol) and 1,3-dibromopropane (3.05 mL, 30.0 mmol) in anhydrous DMF (20 mL) at ambient temperature under nitrogen; The mixture is heated at 80° C. for 1 hour. At ambient temperature, EtOAc (100 mL) and water (150 mL) are added to the mixture. The organic layer is separated, dried over MgSO4, filtered and concentrated. The crude product is chromatographed on silica (gradient 0-2% EtOAc in hexane) to give 2.45 g (7.21 mmol, 72% yield) of the title compound as a white solid. EIMS: m/z 338 (M+, 35Cl, 79Br), 340 (M+, 37Cl, 37Br or 35Cl, 81Br), 342 (M+, 37Cl, 81Br).

Workup

  1. customThe organic layer is separated
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product is chromatographed on silica (gradient 0-2% EtOAc in hexane)

Sources & evidence

ORD record
ord-c61ba92ccbaa4c6a8a057eb75c6a9d8b
Source dataset
uspto-grants-2008_08
Patent number
US07414063B2

Reaction notes

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