Dimethylformamide → 1-Bromo-4-(2-chloroethoxy)benzene

HRID 1099544Notes

Reaction equation

HRID 1099544 reaction equation
C(=O)([O-])[O-].[K+].[K+].CN(C=O)C.[Br:12][C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1.CC1C=CC(S(O[CH2:31][CH2:32][Cl:33])(=O)=O)=CC=1>O>[Br:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:31][CH2:32][Cl:33])=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6639Ethanol, 2-chloro-, 1-(4-methylbenzenesulfonate)HCID 78084-BromophenolHCID 11430Potassium Carbonate

Product 1

HCID 1086801-Bromo-4-(2-chloroethoxy)benzeneYield 86%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
10 °C

Procedure

With reference to the document (J. Org. Chem., (2002), 67, 1093-1101), potassium carbonate (83.0 g, 600 mmol) was added to a solution of DMF (500 mL) containing 4-bromophenol (50.4 g, 291 mmol) at room temperature. The mixture was stirred at the same temperature for 30 minutes, and then 2-chloroethyl 4-methylbenzenesulfonate (70.2 g, 299 mmol) was added thereto. The mixture was stirred at 50° C. for 24 hours. The reaction solution was cooled to 10° C., and water (500 mL) was added thereto to precipitate a white solid. This white solid was collected by filtration, washed with water (500 mL), and dried at 50° C. under reduced pressure to give 58.6 g of the title compound (yield: 86%).

Workup

  1. stirringThe mixture was stirred at 50° C. for 24 hours
  2. customto precipitate a white solid
  3. filtrationThis white solid was collected by filtration
  4. washwashed with water (500 mL)
  5. customdried at 50° C. under reduced pressure

Sources & evidence

ORD record
ord-bc2681647bf944feaab5977d4675e32d
Source dataset
uspto-grants-2012_03
Patent number
US08143446B2

Reaction notes

Loading…