Potassium Carbonate → 1-(4-Bromophenoxy)-2-(2,6-dichloro-4-methylphenoxy)ethane

HRID 2428084Notes

Reaction equation

HRID 2428084 reaction equation
C([O-])([O-])=O.[K+].[K+].[Cl:7][C:8]1[C:13]([OH:14])=[C:12]([Cl:15])[CH:11]=[C:10]([CH3:16])[CH:9]=1.[Br:17][C:18]1[CH:31]=[CH:30][C:21]([O:22][CH2:23][CH2:24]OS(C)(=O)=O)=[CH:20][CH:19]=1>O.C(O)CC>[Br:17][C:18]1[CH:31]=[CH:30][C:21]([O:22][CH2:23][CH2:24][O:14][C:13]2[C:8]([Cl:7])=[CH:9][C:10]([CH3:16])=[CH:11][C:12]=2[Cl:15])=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 170772,6-Dichloro-4-methylphenolHCID 532566762-(4-Bromophenoxy)ethyl methanesulfonate

Product 1

HCID 498559311-(4-Bromophenoxy)-2-(2,6-dichloro-4-methylphenoxy)ethaneYield 81.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 10311-PropanolSolvent2×

Conditions

Temperature
85 °C

Procedure

K2CO3 (29.3 g, 212 mmol) was dissolved in water (162 mL). 1-Propanol (150 mL) was added. A sol. of 2,6-dichloro-para-cresol (25 g, 141 mmol) in 1-propanol (150 mL) was added. Methanesulfonic acid 2-(4-bromo-phenoxy)-ethyl ester (41.6 g, 141 mmol) was added. The mixture was stirred at 85° C. for 6 h. The heating oil bath was removed, and water (330 mL) was added dropwise when the internal temperature had reached 78° C. The beige suspension was allowed to cool to rt. The mixture was filtered, and the precipitate was washed with water. Drying the precipitate under high vacuum at 30° C. for 48 h yielded the title compound (43 g, 81%). LC-MS: tR=1.15 min.

Workup

  1. customThe heating oil bath was removed
  2. additionwater (330 mL) was added dropwise when the internal temperature
  3. customhad reached 78° C
  4. temperatureto cool to rt
  5. filtrationThe mixture was filtered
  6. washthe precipitate was washed with water
  7. customDrying the precipitate under high vacuum at 30° C. for 48 h

Sources & evidence

ORD record
ord-468bd9f2c83147eb9d91d7fde0c97f45
Source dataset
uspto-grants-2011_06
Patent number
US07968720B2

Reaction notes

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