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

HRID 1946344Notes

Reaction equation

HRID 1946344 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[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]=[C:5]([N+:8]([O-:10])=[O:9])[CH:6]=[CH:7][C:2]=1[CH3:1]

Participants

5

Reactant 3

HCID 24614Phosphorus tribromideHCID 516892Sodium BicarbonateHCID 3567085(2-Methyl-5-nitrophenyl)methanol

Product 1

HCID 509991612-(Bromomethyl)-1-methyl-4-nitrobenzeneYield 65.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a slight suspension of (2-methyl-5-nitrophenyl)methanol (2.0 g, 12 mmol) in DCM (20 ml) in an ice-water bath under nitrogen was a added a solution of phosphorus tribromide (1.13 mL, 12 mmol, Aldrich) in DCM (20 ml). The resulting solution was allowed to warm to ambient temperature and stirred for 45 min. The solution was poured onto a mixture of ice-water (50 ml) and saturated sodium hydrogen carbonate (50 ml). The biphasic mixture was diluted with dichloromethane (50 ml) and the phases separated. The aqueous phase was extracted with dichloromethane (20 ml). The combined organic extracts were dried (MgSO4), filtered and the solvent removed in vacuo to give 2-(bromomethyl)-1-methyl-4-nitrobenzene as a pale yellow solid (1.81 g).

Workup

  1. customthe phases separated
  2. extractionThe aqueous phase was extracted with dichloromethane (20 ml)
  3. dry with materialThe combined organic extracts were dried (MgSO4)
  4. filtrationfiltered
  5. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-238a4e5248be4c31b67678f9d92a5e07
Source dataset
uspto-grants-2013_03
Patent number
US08399436B2

Reaction notes

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