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

HRID 1373754Notes

Reaction equation

HRID 1373754 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.[CH2:12](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[CH2:12]([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:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 243644-Bromo-2-nitrophenol

Product 1

HCID 112782421-(Benzyloxy)-4-bromo-2-nitrobenzeneYield 96%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 4-bromo-2-nitro-phenol (5.05 g, 23.16 mmol), benzyl bromide (4.12 mL, 34.73 mmol) and K2CO3 (9.60 g, 69.48 mmol) in acetone (200 mL) were stirred, and refluxed for 3 hours. The solution was filtered, dried with silica gel powder (20 g), and separated by flash chromatography eluting with 5% ethyl acetate in hexanes (1 L) and then with 20% ethyl acetate in hexanes (1 L) to give the title compound (6.84 g, 96%). MS (DCI) m/z 326.90 (M+NH4)+; 1H NMR (500 MHz, CD2Cl2) δ ppm 5.21 (s, 2 H) 7.06 (d, J=9.05 Hz, 1 H) 7.33–7.46 (m, 5 H) 7.63 (dd, J=8.73, 2.50 Hz, 1 H) 7.97 (d, J=2.50 Hz, 1 H).

Workup

  1. temperaturerefluxed for 3 hours
  2. filtrationThe solution was filtered
  3. customdried with silica gel powder (20 g)
  4. customseparated by flash chromatography
  5. washeluting with 5% ethyl acetate in hexanes (1 L)

Sources & evidence

ORD record
ord-d431e52aec1340d0a5faabcd8a71f327
Source dataset
uspto-grants-2007_01
Patent number
US07163939B2

Reaction notes

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