1,3-Dibromopropane → 1-(3-bromopropoxy)-4-phenoxy-2-propylBenzene

HRID 2185032Notes

Reaction equation

HRID 2185032 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[C:10]([CH2:15][CH2:16][CH3:17])[CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:18][CH2:19][CH2:20][CH2:21]Br.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[C:2]1([O:1][C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:21][CH2:20][CH2:19][Br:18])=[C:10]([CH2:15][CH2:16][CH3:17])[CH:9]=2)[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 80011,3-DibromopropaneHCID 10796Cesium carbonateHCID 154629044-Phenoxy-2-propylphenol

Product 1

HCID 187722731-(3-bromopropoxy)-4-phenoxy-2-propylBenzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-phenoxy-2-propylphenol (12.0 g, 52.60 mmol), 1,3-dibromopropane ( 31.86 g, 157.81 mmol) and cesium carbonate (18.0 g, 55.23 mmol) in dry DMF ( 110 mL) was stirred at room temperature overnight. The reaction mixture was partitioned between ethyl acetate and 0.2N HCl. The organic was washed twice with water, then dried over sodium sulfate. The organic was filtered and evaporated to an oil which was chromatographed over silica gel with methylene chloride/hexane (1:1) to afford the title compound.

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and 0.2N HCl
  2. washThe organic was washed twice with water
  3. dry with materialdried over sodium sulfate
  4. filtrationThe organic was filtered
  5. customevaporated to an oil which
  6. customwas chromatographed over silica gel with methylene chloride/hexane (1:1)

Sources & evidence

ORD record
ord-dbc3971fbb444e4a9108563ea3bddbb7
Source dataset
uspto-grants-2002_06
Patent number
US06399640B1

Reaction notes

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