Water → HCID 836416, compound

HRID 1861955Notes

Reaction equation

HRID 1861955 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH2:7]Br)([O-:3])=[O:2].C([N:15](C(C)C)CC)(C)C.[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.O>CO>[N+:1]([C:4]1[CH:5]=[C:6]([CH2:7][NH:15][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:9]=[CH:10][CH:11]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 77568Benzene, 1-(bromomethyl)-3-nitro-HCID 81531Diisopropylethylamine

Product 1

HCID 836416HCID 836416, compoundYield 79.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of m-nitrobenzyl bromide (1.0 g) and diisopropylethylamine (1.19 g) in methanol (50 ml), benzyl bromide (495 mg) was added dropwise under ice cooling. The reaction mixture was stirred at room temperature for 3 days and, after addition of water, extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, dried with anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent, n-hexane:ethyl acetate=4:1) to give 555 mg of the titled compound (yield, 50%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  3. dry with materialdried with anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (eluent, n-hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-dcbbb72ed544405393f5e34795f5b619
Source dataset
uspto-grants-2003_03
Patent number
US06534546B1

Reaction notes

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