Dimethylformamide → 1,3-Dibromo-2-(2-chloroethoxy)-5-fluorobenzene

HRID 928643Notes

Reaction equation

HRID 928643 reaction equation
CN(C=O)C.Br[CH2:7][CH2:8][Cl:9].C(=O)([O-])[O-].[K+].[K+].[Br:16][C:17]1[CH:22]=[C:21]([F:23])[CH:20]=[C:19]([Br:24])[C:18]=1[OH:25]>C(OCC)(=O)C>[Br:16][C:17]1[CH:22]=[C:21]([F:23])[CH:20]=[C:19]([Br:24])[C:18]=1[O:25][CH2:7][CH2:8][Cl:9]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 78491-Bromo-2-ChloroethaneHCID 11430Potassium CarbonateHCID 676542,6-Dibromo-4-fluorophenol

Product 1

HCID 108304061,3-Dibromo-2-(2-chloroethoxy)-5-fluorobenzeneYield 56%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

DMF (50 mL), 1-bromo-2-chloroethane (1.0 mL, 12 mmol), and potassium carbonate (1.7 g, 12 mmol) were added to 2,6-dibromo-4-fluorophenol (3.0 g, 11 mmol), and stirred at 50° C. overnight. Ethyl acetate was used as an extraction solvent, and after washing with water and saturated brine, and the resultant was dried over magnesium sulfate. The solvent was distilled away under reduced pressure. The resulting residue was purified by silica gel column chromatography to thus obtain the title compound.

Workup

  1. washafter washing with water and saturated brine
  2. dry with materialthe resultant was dried over magnesium sulfate
  3. distillationThe solvent was distilled away under reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-e6e5b6ac665147d0a951ee8243fb0b58
Source dataset
uspto-grants-2016_03
Patent number
US09290487B2

Reaction notes

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