Triphenylphosphine → 1-(Bromomethyl)-3-methyl-2-nitrobenzene

HRID 2211880Notes

Reaction equation

HRID 2211880 reaction equation
[CH3:1][C:2]1[C:3]([N+:10]([O-:12])=[O:11])=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Br:51]Br>C(#N)C>[CH3:1][C:2]1[C:3]([N+:10]([O-:12])=[O:11])=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][Br:51]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 5619893-Methyl-2-nitrobenzenemethanolHCID 44191054Bromine triphenylphosphine

Product 1

HCID 129324351-(Bromomethyl)-3-methyl-2-nitrobenzene

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

A round bottomed flask was charged with 5.0 g (0.029 mol) of 3-methyl-2-nitrobenzyl alcohol and 100 mL of anhydrous acetonitrile. The reaction solution was cooled to 0° C. and treated, portionwise, with 13.2 g (0.031 mol) triphenylphosphine perbromide (Ph3P—Br2). The reaction was allowed to warm to rt overnight at which point the solvent was removed and the resulting solids triturated with 50:50 ether:hexanes. The wash solvent was filtered through a fine frit and then concentrated to give a quantitative yield (7.03 g) of the desired material as a white solid. 1H NMR (400 MHz, CDCl3) δ 7.36–7.34 (m, 2H), 7.33–7.24 (m, 1H), 4.45 (s, 2H), 2.33 (s, 3H).

Workup

  1. additiontreated
  2. temperatureto warm to rt overnight at which point the solvent
  3. customwas removed
  4. customthe resulting solids triturated with 50:50 ether
  5. filtrationThe wash solvent was filtered through a fine frit
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-1a1d0e9df3b84acab47805fc88582000
Source dataset
uspto-grants-2006_09
Patent number
US07101886B2

Reaction notes

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