1-Bromo-3-chloropropane → HCID 16789618, compound

HRID 1801485Notes

Reaction equation

HRID 1801485 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([C:9]#[N:10])[CH:6]=[CH:5][C:4]=1[OH:11].C([O-])([O-])=O.[K+].[K+].[Cl:18][CH2:19][CH2:20][CH2:21]Br>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH:6]=[CH:5][C:4]=1[O:11][CH2:21][CH2:20][CH2:19][Cl:18])[C:9]#[N:10]

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 781354-Hydroxy-3-methoxybenzonitrile

Product 1

HCID 16789618HCID 16789618, compoundYield 103%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
37 °C

Procedure

2-methoxy-4-cyano-phenol (0.25 g, 1.67 mmol) and anhydrous DMF (2.00 mL) were added into a round bottom flask. The solution was stirred and cooled in a water bath. Several batches of anhydrous K2CO3 (0.347 g, 2.50 mmol) were added to the solution and the mixture was stirred at 20° C. to react for 1 h. 1-chloro-3-bromopropane (0.23 ml, 2.14 mmol) was added, and the mixture was stirred at room temperature (25° C.) to react overnight. The mixture was heated to 37° C. to react for 6 h and then poured into a mixture of ice/H2O (25 mL). After stirring for 10 min, a precipitate was formed. Filtered, washed with H2O, and air-dried to yield white solid product (0.388 g) with a recovery rate of 90%.

Workup

  1. temperaturecooled in a water bath
  2. stirringthe mixture was stirred at 20° C.
  3. customto react for 1 h
  4. stirringthe mixture was stirred at room temperature (25° C.)
  5. customto react overnight
  6. customto react for 6 h
  7. stirringAfter stirring for 10 min
  8. customa precipitate was formed
  9. filtrationFiltered
  10. washwashed with H2O
  11. customair-dried

Sources & evidence

ORD record
ord-3a0c1d26053240aa98cbcf1b634b1066
Source dataset
uspto-grants-2013_01
Patent number
US08349835B2

Reaction notes

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