Benzene, 1-(bromomethyl)-3-nitro- → HCID 63282031, compound

HRID 2171213Notes

Reaction equation

HRID 2171213 reaction equation
[Cl-].[OH:2][CH:3]1[CH2:6][NH2+:5][CH2:4]1.CCN(C(C)C)C(C)C.Br[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([N+:24]([O-:26])=[O:25])[CH:19]=1>C(#N)C>[N+:24]([C:20]1[CH:19]=[C:18]([CH:23]=[CH:22][CH:21]=1)[CH2:17][N:5]1[CH2:6][CH:3]([OH:2])[CH2:4]1)([O-:26])=[O:25]

Participants

5

Reactant 3

HCID 77568Benzene, 1-(bromomethyl)-3-nitro-HCID 81531DiisopropylethylamineHCID 4488865218621-18-6

Product 1

HCID 63282031HCID 63282031, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 3-hydroxyazetidinium chloride (0.68 g, 6.2 mmol) and Hunig's base (2.5 mL, 14.1 mmol) in acetonitrile (10 ml) was added 1-(bromomethyl)-3-nitrobenzene. After the reaction mixture was stirred at room temperature for 18 hours, it was partitioned between ethyl acetate and NaHCO3. The organic layer was washed with brine, dried and concentrated. The crude material was purified by silica gel column chromatography, eluting with 20% ethyl acetate/hexanes to give 0.54 g 1-(3-nitrobenzyl)azetidin-3-ol. MS (DCI(+)) m/e 209 (M+H)+.

Workup

  1. customit was partitioned between ethyl acetate and NaHCO3
  2. washThe organic layer was washed with brine
  3. customdried
  4. concentrationconcentrated
  5. customThe crude material was purified by silica gel column chromatography
  6. washeluting with 20% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-de95c121a5c546e6b738f9c980497539
Source dataset
uspto-grants-2015_06
Patent number
US09051315B2

Reaction notes

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