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

HRID 1799234Notes

Reaction equation

HRID 1799234 reaction equation
C(=O)([O-])[O-].[K+].[K+].CN(C)C=O.[Br:12][C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1.C1(C)C=CC(S(O[CH2:30][CH2:31][Cl:32])(=O)=O)=CC=1>O>[Br:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:30][CH2:31][Cl:32])=[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
110 °C

Procedure

The preparation was conducted according to the description in the document (J. Org. Chem., (2002), 67, 1093-1101). Potassium carbonate (83.0 g, 600 mmol) was added to an N,N-dimethylformamide (DMF, 500 mL) solution of 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 p-toluenesulfonate (70.2 g, 299 mmol) was added thereto. The resulting mixture was stirred at 50° C. for 24 hours. The reaction solution was cooled to 110° C., and water (500 mL) was added thereto to precipitate a white solid. The solid was collected by filtration, washed with water (500 mL), and dried under reduced pressure to give 58.6 g of the title compound (white powder, yield: 86%).

Workup

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

Sources & evidence

ORD record
ord-8c32acbc95cc4ef5b5eef0ca8fab8b6a
Source dataset
uspto-grants-2013_01
Patent number
US08344029B2

Reaction notes

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