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

HRID 1441437Notes

Reaction equation

HRID 1441437 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH2:18](Cl)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CN(C=O)C>[CH2:18]([O:8][C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][C:4]=1[N+:9]([O-:11])=[O:10])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 243644-Bromo-2-nitrophenol

Product 1

HCID 112782421-(Benzyloxy)-4-bromo-2-nitrobenzeneYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

4-Bromo-2-nitro-phenol (Aldrich, 2.18 g, 10 mmol) was treated with K2CO3 (Aldrich, 2.76 g, 20 mmol) in DMF (Aldrich, 100 mL) at ambient temperature for 20 min. Benzyl chloride (Aldrich, 1.52 g, 12 mmol) was added. The mixture was stirred at 100° C. for 6 h. It was then poured into ice/water (200 mL) and stirred at ambient temperature for 10 hours. The white solid was filtered and dried to give the title compound (3.0 g, yield, 100%). 1H NMR (300 MHz, CDCl3) δ 5.23 (s, 2H), 7.01 (d, J=9.2 Hz, 1H), 7.31-7.49 (m, 5H), 7.58 (dd, J=9.0, 2.5 Hz, 1H), 7.98 (d, J=2.7 Hz, 1H) ppm. MS (DCI/NH3): 325 (M+H)+, 327 (M+H)+.

Workup

  1. stirringstirred at ambient temperature for 10 hours
  2. filtrationThe white solid was filtered
  3. customdried

Sources & evidence

ORD record
ord-8dfc4a8708324e998f1b8975aa6ee775
Source dataset
uspto-grants-2010_02
Patent number
US07655657B2

Reaction notes

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