Benzyl Bromide → 1-(Benzyloxy)-2-bromo-4-nitrobenzene

HRID 565377Notes

Reaction equation

HRID 565377 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[OH:11].[CH2:12](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C)C=O.O>[CH2:12]([O:11][C:3]1[CH:4]=[CH:5][C:6]([N+:8]([O-:10])=[O:9])=[CH:7][C:2]=1[Br:1])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

7

Reactant 4

HCID 7498Benzyl BromideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 221092-Bromo-4-nitrophenol

Product 1

HCID 220178401-(Benzyloxy)-2-bromo-4-nitrobenzeneYield 89.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 2-bromo-4-nitrophenol (Description 6; 14 g, 68.6 mmol), benzyl bromide (14.1 g, 82.4 mmol) and potassium carbonate (47.3 g, 0.343 mol) in dimethylformamide (100 ml) was heated at 60° C. for 3 hours. The mixture was cooled to room temperature and poured into a mixture of ethyl acetate and water. The organic phase was washed with water (3 times) and saturated brine, dried (MgSO4) and the solvent was evaporated under reduced pressure. The residue was recrystallized from methanol to give the title compound (19 g). H NMR (250 MHz, CDCl3) δ 8.48 (1H, d, J 2.8 Hz), 8.18 (1H, dd, J 9.08 Hz, 2.8 Hz), 7.46−7.3 (5H, m), 7.0 (1H, d, J 9.2 Hz), and 5.27 (2H, s).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. washThe organic phase was washed with water (3 times) and saturated brine
  3. dry with materialdried (MgSO4)
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was recrystallized from methanol

Sources & evidence

ORD record
ord-d48889c19499432bad79ffa7bb83d158
Source dataset
uspto-grants-2001_01
Patent number
US06172077B2

Reaction notes

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