Water → 2-(Bromomethyl)-4-methoxy-1-nitrobenzene

HRID 1242852Notes

Reaction equation

HRID 1242852 reaction equation
O.[CH3:2][O:3][C:4]1[CH:5]=[CH:6][C:7]([N+:11]([O-:13])=[O:12])=[C:8]([CH3:10])[CH:9]=1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.[Br:32]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:32][CH2:10][C:8]1[CH:9]=[C:4]([O:3][CH3:2])[CH:5]=[CH:6][C:7]=1[N+:11]([O-:13])=[O:12]

Participants

6

Reactant 4

HCID 962WaterHCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 793303-Methyl-4-nitroanisole

Product 1

HCID 124231262-(Bromomethyl)-4-methoxy-1-nitrobenzeneYield 47%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

The reaction apparatus consisted of a 50-mL single-necked round-bottom flask equipped with a water-jacketed condensor, magnetic stirrer, and an argon-filled balloon. A solution of 5-methoxy-2-nitrotoluene (0.25 g, 1.50 mmol), carbon tetrachloride (25 mL), a catalytic amount of benzoyl peroxide (25 mg, 0.83 mmol), and N-bromosuccinimide (0.32 g, 1.8 mmol) were added to the reaction flask. The mixture was refluxed and irradiated under a 90-watt lamp (GE watt-miser light bulb, 130 V, 1000 hrs) for 5 h and then cooled to room temperature. The precipitated succinimide was removed by gravity filtration and the filtrate was extracted with sodium metabisulfite (28 M, 1×50 mL) and water (1×50 mL). The organic layer was separated, dried over sodium sulfate, filtered and then evaporated to afford a crude oil (382 mg, 105%). The crude product was chromatographed on silica gel (hexane/EtOAc=9:1) to give the product as yellow crystals (172 mg, 47%): m.p. 64–65° C.

Workup

  1. customThe reaction apparatus consisted of a 50-mL single-necked round-bottom flask
  2. additionan argon-filled balloon
  3. temperatureThe mixture was refluxed
  4. customirradiated under a 90-watt lamp (GE watt-miser light bulb, 130 V, 1000 hrs) for 5 h
  5. customThe precipitated succinimide was removed by gravity filtration
  6. extractionthe filtrate was extracted with sodium metabisulfite (28 M, 1×50 mL) and water (1×50 mL)
  7. customThe organic layer was separated
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. customevaporated
  11. customto afford a crude oil (382 mg, 105%)
  12. customThe crude product was chromatographed on silica gel (hexane/EtOAc=9:1)

Sources & evidence

ORD record
ord-f0f211fd604849fa85a75399692f58f8
Source dataset
uspto-grants-2006_10
Patent number
US07115766B2

Reaction notes

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