Sodium hydride → HCID 22014403, compound

HRID 1532764Notes

Reaction equation

HRID 1532764 reaction equation
[H-].[Na+].[C:3]([C:5]1[CH:6]=[CH:7][C:8]([N+:12]([O-:14])=[O:13])=[C:9]([OH:11])[CH:10]=1)#[N:4].Br[CH2:16][O:17][CH3:18]>C1COCC1>[C:3]([C:5]1[CH:6]=[CH:7][C:8]([N+:12]([O-:14])=[O:13])=[C:9]([O:11][CH2:16][O:17][CH3:18])[CH:10]=1)#[N:4]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 83093Bromomethyl methyl etherHCID 151119213-Hydroxy-4-nitrobenzonitrile

Product 1

HCID 22014403HCID 22014403, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To sodium hydride (60% oil dispersion, 260 mg, 6.5 mmol), previously washed with hexanes, in THF (5 ml) was added dropwise at rt 5-cyano-2-nitro-phenol (978 mg, 5.96 mmol) in THF (10 ml). The solution turned bright orange and a large prepipitate formed. After stirring 15 min at rt bromomethylmethylether was added dropwise to this stirred slurry and the reaction was stirred for 18 h at rt. The yellow-colored mixture was then partitioned between t-butyl-O-methylether and water and the aqueous portion was extracted (×3) and washed with 5% sodium bicarbonate solution (×4) and brine. After drying (MgSO4), filtration and evaporation under reduced pressure afforded the title compound as a pale yellow solid (1.05 g, 85%).1H NMR(400 MHz, CDCl3) δ 7.84 (d, J=8.4 Hz, 1H), 7.66 (d, J=1.4 Hz 1H), 7.35 (dd, J=8.4 Hz J=1.5 Hz, 1H), 5.34 (s, 2H), 3.55 (s, 3H).

Workup

  1. customa large prepipitate formed
  2. additionwas added dropwise to this stirred slurry
  3. customThe yellow-colored mixture was then partitioned between t-butyl-O-methylether and water
  4. extractionthe aqueous portion was extracted (×3)
  5. washwashed with 5% sodium bicarbonate solution (×4) and brine
  6. customAfter drying
  7. filtration(MgSO4), filtration and evaporation under reduced pressure

Sources & evidence

ORD record
ord-7ebd24d606ed429c8f28e5289a56e527
Source dataset
uspto-grants-2001_03
Patent number
US06204294B1

Reaction notes

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