1-Bromo-3-chloropropane → HCID 21701922, compound

HRID 1596471Notes

Reaction equation

HRID 1596471 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:11]=1[OH:12])[C:7]#[N:8].Br[CH2:14][CH2:15][CH2:16][Cl:17]>CN(C=O)C>[Cl:17][CH2:16][CH2:15][CH2:14][O:12][C:11]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][C:4]=1[OH:3]

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 24758Sodium hydrideHCID 870653,4-Dihydroxybenzonitrile

Product 1

HCID 21701922HCID 21701922, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

NaH (0.20 g; 8.14 mmol) was added to a room temperature solution of 3,4-dihydroxybenzonitrile (1.00 g; 7.40 mmol) in DMF. After stirring for 15 minutes, 1-bromo-3-chloropropane (1.3 g; 8.14 mmol) was added to the mixture. The reaction was stirred for 40 h at room temperature, and then quenched with water and extracted with EtOAc (100 mL). The EtOAc extract was washed with brine (4×100 mL), dried over Na2SO4 and concentrated in vacuo. The resulting crude product was chromatographed on a column of silica (5 cm×18 cm) eluting with a mixture of EtOAc and hexanes (1:4). Fractions containing the desired product were combined and concentrated in vacuo to afford the sub-title compound as an oil (0.5 g; 32%).

Workup

  1. stirringThe reaction was stirred for 40 h at room temperature
  2. customquenched with water
  3. extractionextracted with EtOAc (100 mL)
  4. extractionThe EtOAc extract
  5. washwas washed with brine (4×100 mL)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customThe resulting crude product was chromatographed on a column of silica (5 cm×18 cm)
  9. washeluting with a mixture of EtOAc and hexanes (1:4)
  10. additionFractions containing the desired product
  11. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cca36c7c936f46b8a6bd20cff14092ee
Source dataset
uspto-grants-2001_09
Patent number
US06291475B1

Reaction notes

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