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

HRID 731968Notes

Reaction equation

HRID 731968 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 66.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A stirred solution of 7.5 grams (0.028 mole) of 2,6-dichloro-4-phenylmethoxyphenol (known compound) and 3 mL (0.030 mole) of 1-bromo-4-chlorobutane in 225 mL of DMF was cooled in an ice bath, and 5.8 grams (0.042 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 6.7 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-96bedba2dbe54b17a2b5b72e8407f4dd
Source dataset
uspto-grants-2009_09
Patent number
US07585891B2

Reaction notes

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