Calcium Carbonate → HCID 22648003, compound

HRID 394081Notes

Reaction equation

HRID 394081 reaction equation
Br[CH2:2][C:3]1[C:8]([Br:9])=[CH:7][C:6]([N+:10]([O-:12])=[O:11])=[CH:5][C:4]=1[Br:13].C([O-])([O-])=[O:15].[Ca+2]>O1CCOCC1.O>[OH:15][CH2:2][C:3]1[C:8]([Br:9])=[CH:7][C:6]([N+:10]([O-:12])=[O:11])=[CH:5][C:4]=1[Br:13]

Participants

5

Reactant 2

HCID 10112Calcium CarbonateHCID 22648021HCID 22648021, compound

Product 1

HCID 22648003HCID 22648003, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 1-bromomethyl-2,6-dibromo-4-nitrobenzene (4.45 g, 1 eq.) and CaCO3 (5.7 g, 5 eq.) in 1,4-dioxane (20 mL) and water (20 mL) was heated to and maintained at reflux overnight. The mixture was cooled, poured into water and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrousmgSO4, filtered and concentrated. The product was purified by silica gel chromatography (eluted with 4:1 hexanes:ethyl acetate) to give 1-Hydroxymethyl-2,6-dibromo-4-nitrobenzene. 1H NMR (500 MHz, CDCl3) δ CHCl3: 2.28 (1H, broad t), 5.05(2H, m), 8.397(2H, s).

Workup

  1. temperaturewas heated to and
  2. temperaturemaintained
  3. temperatureat reflux overnight
  4. temperatureThe mixture was cooled
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with brine
  7. customdried over anhydrousmgSO4,
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe product was purified by silica gel chromatography (eluted with 4:1 hexanes:ethyl acetate)

Sources & evidence

ORD record
ord-0b20ce1b46394d309386f5b920be8c26
Source dataset
uspto-grants-2004_10
Patent number
US06809199B2

Reaction notes

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