Dimethylformamide → HCID 66602625, compound

HRID 2097467Notes

Reaction equation

HRID 2097467 reaction equation
CN(C)C=O.[Br:6][C:7]1[CH:8]=[CH:9][C:10]([O:14][CH3:15])=[C:11]([OH:13])[CH:12]=1.Br[CH2:17][CH2:18][Cl:19].C(=O)([O-])[O-].[K+].[K+]>O>[Br:6][C:7]1[CH:8]=[CH:9][C:10]([O:14][CH3:15])=[C:11]([O:13][CH2:17][CH2:18][Cl:19])[CH:12]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 78491-Bromo-2-Chloroethane2×HCID 11430Potassium Carbonate2×HCID 1422285-Bromo-2-methoxyphenol

Product 1

HCID 66602625HCID 66602625, compoundYield 103.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

To 1.2 L of N,N-dimethylformamide solution containing 159 g (0.79 mol) of 5-bromo-2-methoxyphenol (see WO 01019785) were added 340 g (2.37 mol) of 1-bromo-2-chloroethane and 120 g (0.868 mol) of potassium carbonate, and the mixture was stirred at 70° C. for 5 hours. Then, 220 g (1.53 mol) of 1-bromo-2-chloroethane and 80 g (0.58 mol) of potassium carbonate were additionally added thereto twice by dividing them to two portions during the reaction, and the mixture was further stirred for 7 hours. After completion of the reaction, the reaction mixture was poured into water, and extracted with toluene. The organic layer after separation was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain 217 g of the title compound as a dark brownish solid substantially quantitatively.

Workup

  1. customduring the reaction
  2. stirringthe mixture was further stirred for 7 hours
  3. customAfter completion of the reaction
  4. extractionextracted with toluene
  5. customThe organic layer after separation
  6. washwas washed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e168130c8da24c38972e4328c18e46c3
Source dataset
uspto-grants-2013_05
Patent number
US08450319B2

Reaction notes

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