Phosphorus tribromide → 4-(Bromomethyl)-1-methoxy-2-nitrobenzene

HRID 1826097Notes

Reaction equation

HRID 1826097 reaction equation
P(Br)(Br)[Br:2].[CH3:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13]O)=[CH:9][C:8]=1[N+:15]([O-:17])=[O:16]>CCOCC>[Br:2][CH2:13][C:10]1[CH:11]=[CH:12][C:7]([O:6][CH3:5])=[C:8]([N+:15]([O-:17])=[O:16])[CH:9]=1

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 4432413(4-Methoxy-3-nitrophenyl)methanol

Product 1

HCID 115796484-(Bromomethyl)-1-methoxy-2-nitrobenzeneYield 137.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Under an argon atmosphere and cooling with ice, phosphorus tribromide (2.36 mL, 24.7 mmol) was added dropwise to a solution of (4-methoxy-3-nitrophenyl)methanol (12.2 g, 66.6 mmol) in anhydrous ether (350 mL) under stirring, and the mixture was stirred for 3.5 hours. Ice water (300 mL) was added to the reaction mixture. The organic layer was separated, washed with water and brine, dried over anhydrous sodium sulfate, and then concentrated. The residue was purified by means of silica gel column chromatography (eluent: n-hexane:ethyl acetate=2:1→1:1 v/v) to afford 8.36 g (51%) of the title compound as pale yellow crystals.

Workup

  1. stirringthe mixture was stirred for 3.5 hours
  2. customThe organic layer was separated
  3. washwashed with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by means of silica gel column chromatography (eluent: n-hexane:ethyl acetate=2:1→1:1 v/v)

Sources & evidence

ORD record
ord-782bb76086ec4ceb8d9890bc5c21fab4
Source dataset
uspto-grants-2006_05
Patent number
US07049342B2

Reaction notes

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