1-Bromopropane → HCID 86669352, compound

HRID 401194Notes

Reaction equation

HRID 401194 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[C:9]=1[OH:10])[CH:5]=[O:6].[C:14]([O-])([O-])=O.[K+].[K+].Br[CH2:21][CH2:22][CH3:23].C(O[CH2:28][CH3:29])(=O)C>CN(C=O)C>[N+:11]([C:8]1[CH:7]=[C:4]([CH:3]=[C:2]([O:1][CH2:14][CH2:28][CH3:29])[C:9]=1[O:10][CH2:21][CH2:22][CH3:23])[CH:5]=[O:6])([O-:13])=[O:12]

Participants

6

Reactant 4

HCID 78401-BromopropaneHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 57489573,4-Dihydroxy-5-nitrobenzaldehyde

Product 1

HCID 86669352HCID 86669352, compoundYield 32.91%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 3,4-dihydroxy-5-nitrobenzaldehyde (400 mg, 2.185 mmol) in DMF (5 mL) was added K2CO3 (603 mg, 4.37 mmol) and 1-bromopropane (0.5 mL, excess), and the reaction was stirred at 80° C. overnight. Ethyl acetate (100 mL) was added and was washed with 2N aqueous HCl solution (20 mL×1), brine (20 mL×3), dried over Na2SO4, filtered, concentrated. The residue was purified by column chromatography (192 mg, yield: 32.91%).

Workup

  1. washwas washed with 2N aqueous HCl solution (20 mL×1), brine (20 mL×3)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography (192 mg, yield: 32.91%)

Sources & evidence

ORD record
ord-b4684e16f91f471db8903a36201727b6
Source dataset
uspto-grants-2014_06
Patent number
US08741915B2

Reaction notes

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