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

HRID 1946323Notes

Reaction equation

HRID 1946323 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[CH2:11]O.P(Br)(Br)[Br:14].C(=O)([O-])O.[Na+]>C(Cl)Cl>[Br:14][CH2:11][C:3]1[CH:4]=[CH:5][C:6]([N+:8]([O-:10])=[O:9])=[CH:7][C:2]=1[CH3:1]

Participants

5

Reactant 3

HCID 24614Phosphorus tribromideHCID 516892Sodium BicarbonateHCID 21345674(2-Methyl-4-nitrophenyl)methanol

Product 1

HCID 126541471-(Bromomethyl)-2-methyl-4-nitrobenzeneYield 54.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution of (2-methyl-4-nitrophenyl)methanol (2 g, 12 mmol) in DCM (25 ml) in an ice-water bath under nitrogen was added a solution of phosphorous tribromide (1.13 ml, 12 mmol, Aldrich) in DCM (20 ml). The resulting solution was allowed to warm to ambient temperature and stirred for 2 h. The reaction mixture was poured onto ice-water (70 ml) and saturated sodium hydrogen carbonate (30 ml). The mixture was diluted with DCM (50 ml) and the phases separated. The aqueous extract was washed with DCM (20 ml). The combined organic extracts were washed with water (50 ml), dried (MgSO4), filtered and the solvent removed in vacuo to leave 1-(bromomethyl)-2-methyl-4-nitrobenzene as a yellow solid (1.5 g).

Workup

  1. customthe phases separated
  2. extractionThe aqueous extract
  3. washwas washed with DCM (20 ml)
  4. washThe combined organic extracts were washed with water (50 ml)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-34e26a8a2efe4f5b94e98cf1904c7351
Source dataset
uspto-grants-2013_03
Patent number
US08399436B2

Reaction notes

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