1-Bromo-3-chloropropane → HCID 67457441, compound

HRID 1713303Notes

Reaction equation

HRID 1713303 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:5]#[N:6].C(=O)([O-])[O-].[K+].[K+].Br[CH2:23][CH2:24][CH2:25][Cl:26]>CN(C)C=O>[Cl:26][CH2:25][CH2:24][CH2:23][O:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[C:5]#[N:6]

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 21797966HCID 21797966, compound

Product 1

HCID 67457441HCID 67457441, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 3-hydroxy-4-phenylbenzonitrile (3.0 g) in N,N-dimethylformamide (30.7 mL) was added potassium carbonate (6.37 g). Then 1-bromo-3-chloropropane (3.6 mL) was added, and the resulting mixture was stirred at 50° C. for 4 hours. The reaction mixture was partitioned between diethyl ether (45 mL) and water (10 mL). The organic layer was washed with water (10 mL×2) and brine (10 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=15/1) to give the title compound (4.08 g).

Workup

  1. customThe reaction mixture was partitioned between diethyl ether (45 mL) and water (10 mL)
  2. washThe organic layer was washed with water (10 mL×2) and brine (10 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=15/1)

Sources & evidence

ORD record
ord-f23ae4781b5948adb4dda738d95ea382
Source dataset
uspto-grants-2010_09
Patent number
US07795236B2

Reaction notes

Loading…