Dichloromethane → 5-(6-Bromonaphthalen-2-yl)-2,2-dimethyl-5-nitro-1,3-dioxane

HRID 1036386Notes

Reaction equation

HRID 1036386 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]([N+:17]([O-:19])=[O:18])([CH2:15][OH:16])[CH2:13][OH:14])[CH:6]=[CH:5]2.C(Cl)Cl.CO[C:25](OC)([CH3:27])[CH3:26].B(F)(F)F.CCOCC>CCOC(C)=O.CCCCCC>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]1([N+:17]([O-:19])=[O:18])[CH2:15][O:16][C:25]([CH3:27])([CH3:26])[O:14][CH2:13]1)[CH:6]=[CH:5]2

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 64952,2-DimethoxypropaneHCID 8000Boron trifluoride etherateHCID 707005472-(6-Bromonaphthalen-2-yl)-2-nitropropane-1,3-diol

Product 1

HCID 707005465-(6-Bromonaphthalen-2-yl)-2,2-dimethyl-5-nitro-1,3-dioxaneYield 82%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

2-(6-Bromo-naphthalen-2-yl)-2-nitro-propane-1,3-diol (32.6 g, 0.100 mol) was dissolved in methylene chloride (150 mL, 2.3 mol; Acros, anhydrous) and 2,2-dimethoxypropane (180 mL, 1.5 mol; Aldrich), cooled with an ice bath. Boron trifluoride etherate (10.1 mL, 0.0800 mol; Aldrich) was added slowly. The mixture was stirred for 15 min and large amount of solid precipitated. The cooling bath was removed and the mixture was stirred at r.t. for 4 hours. The mixture was quenched with aqueous saturated NaHCO3 (˜600 mL) to pH˜8, extracted with EtOAc (600 mL, 300 mL, 2×100 mL). The EtOAc layer was washed with water, brine, dried over Na2SO4, filtered. The solvent was evaporated to ˜100 mL. The resulted solid product was collected by filtration and the mother liquid was concentrated further to afford the second crop of product. Rf of product=0.4(EtOAc/hexane=1/4). Total product weighed 30.0 g (yield 82%).

Workup

  1. customlarge amount of solid precipitated
  2. customThe cooling bath was removed
  3. stirringthe mixture was stirred at r.t. for 4 hours
  4. customThe mixture was quenched with aqueous saturated NaHCO3 (˜600 mL) to pH˜8
  5. extractionextracted with EtOAc (600 mL, 300 mL, 2×100 mL)
  6. washThe EtOAc layer was washed with water, brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. customThe solvent was evaporated to ˜100 mL
  10. filtrationThe resulted solid product was collected by filtration
  11. concentrationthe mother liquid was concentrated further
  12. customto afford the second crop of product

Sources & evidence

ORD record
ord-0e51a4059f6b4d91a0dc3ed38898f4fc
Source dataset
uspto-grants-2013_10
Patent number
US08546359B2

Reaction notes

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