Sodium Chloride → 1,3-Dichloro-2-(4-chlorobutoxy)-5-(phenylmethoxy)benzene

HRID 1271825Notes

Reaction equation

HRID 1271825 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:5]=[C:4]([Cl:16])[C:3]=1[OH:17].Br[CH2:19][CH2:20][CH2:21][CH2:22][Cl:23].C(=O)([O-])[O-].[K+].[K+].[Cl-].[Na+]>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:5]=[C:4]([Cl:16])[C:3]=1[O:17][CH2:19][CH2:20][CH2:21][CH2:22][Cl:23]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 11430Potassium CarbonateHCID 813641-Bromo-4-chlorobutaneHCID 120841702,6-Dichloro-4-benzyloxyphenol

Product 1

HCID 222571231,3-Dichloro-2-(4-chlorobutoxy)-5-(phenylmethoxy)benzeneYield 80.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A stirred solution of 10.0 grams (0.037 mole) of 2,6-dichloro-4-phenylmethoxyphenol (known compound) and 4.7 grams (0.041 mole) of 1-bromo-4-chlorobutane in 225 mL of DMF was cooled in an ice bath, and 7.7 grams (0.060 mole) of potassium carbonate was added. Upon completion of addition, the reaction mixture was allowed to warm to ambient temperature as it stirred for about 18 hours. The reaction mixture was then poured into 1000 mL of an aqueous solution saturated with sodium chloride. The mixture was extracted with four 150 mL portions of diethyl ether, and the combined extracts were washed with 50 mL of water. The organic layer was dried with sodium sulfate, filtered, and concentrated under reduced pressure to a residue. The residue was purified with column chromatography on silica gel using 1:3 methylene chloride:hexane as an eluant. The appropriate fractions were combined and concentrated under reduced pressure, yielding 10.7 grams of the subject compound. The NMR spectrum was consistent with the proposed structure.

Workup

  1. additionUpon completion of addition
  2. extractionThe mixture was extracted with four 150 mL portions of diethyl ether
  3. washthe combined extracts were washed with 50 mL of water
  4. dry with materialThe organic layer was dried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure to a residue
  7. customThe residue was purified with column chromatography on silica gel using 1:3 methylene chloride
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-19b666e9130a485ca8e18459a40b4a17
Source dataset
uspto-grants-2007_04
Patent number
US07208450B2

Reaction notes

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