Nitromethane → 1-(5-Benzyloxy-2-bromo-phenyl)-2-nitro-ethanol

HRID 1181083Notes

Reaction equation

HRID 1181083 reaction equation
[N+:1]([CH3:4])([O-:3])=[O:2].[OH-].[Na+].[CH2:7]([O:14][C:15]1[CH:16]=[CH:17][C:18]([Br:23])=[C:19]([CH:22]=1)[CH:20]=[O:21])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C(O)C.C(Cl)Cl>[CH2:7]([O:14][C:15]1[CH:16]=[CH:17][C:18]([Br:23])=[C:19]([CH:20]([OH:21])[CH2:4][N+:1]([O-:3])=[O:2])[CH:22]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 3

HCID 6375NitromethaneHCID 14798Sodium HydroxideHCID 108700245-(Benzyloxy)-2-bromobenzaldehyde

Product 1

HCID 179846271-(5-Benzyloxy-2-bromo-phenyl)-2-nitro-ethanol

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of nitromethane (2.02 mL, 37.3 mmol) in ethanol (10 mL) was treated with 10N NaOH (3.0 mL) at ambient temperature. A white solid precipitated immediately, and a solution of 5-benzyloxy-2-bromo-benzaldehyde (8.67 g, 29.8 mmol) in CH2Cl2 (50 mL) was added. The reaction mixture was stirred for 18 h and quenched with water (100 mL). The mixture was extracted with CH2Cl2 (2×50 mL), dried (Na2SO4), and concentrated to a residue, which was then purified by silica gel chromatography (hexanes/EtOAc 8/2) to afford 1-(5-benzyloxy-2-bromo-phenyl)-2-nitro-ethanol as yellow oil.

Workup

  1. customA white solid precipitated immediately
  2. customquenched with water (100 mL)
  3. extractionThe mixture was extracted with CH2Cl2 (2×50 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated to a residue, which
  6. customwas then purified by silica gel chromatography (hexanes/EtOAc 8/2)

Sources & evidence

ORD record
ord-898e0e5f21df46d5b4d74d790cc9c5e1
Source dataset
uspto-grants-2007_10
Patent number
US07282501B2

Reaction notes

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