Toluene → 2-(Bromomethyl)-5-nitrothiophene

HRID 861881Notes

Reaction equation

HRID 861881 reaction equation
P(Br)(Br)[Br:2].O[CH2:6][C:7]1[S:8][C:9]([N+:12]([O-:14])=[O:13])=[CH:10][CH:11]=1.C1(C)C=CC=CC=1>O>[Br:2][CH2:6][C:7]1[S:8][C:9]([N+:12]([O-:14])=[O:13])=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 24614Phosphorus tribromideHCID 332588(5-nitrothiophen-2-yl)methanol

Product 1

HCID 536851562-(Bromomethyl)-5-nitrothiopheneYield 261.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

Phosphorus tribromide (PBr3) (10.45 g) was added dropwise to a mixture of 2-hydroxymethyl-5-nitrothiophene (17.7 g) and toluene (150 ml) and this mixture was stirred at 70° C. for 1.5 hours. The reaction mixture was poured into water and extracted with ether. The ether layer was washed with water and dried (MgSO4), after which the solvent was evaporated off. The residual oil was subjected to solica gel column chromatography and eluted with chloroform to yield 2-bromomethyl-5-nitrothiophene (22.43 g, 92%) as an oil.

Workup

  1. extractionextracted with ether
  2. washThe ether layer was washed with water
  3. dry with materialdried (MgSO4)
  4. customafter which the solvent was evaporated off
  5. washeluted with chloroform

Sources & evidence

ORD record
ord-98cdb1d533454e5390c0078761500449
Source dataset
uspto-grants-1998_02
Patent number
US05716944

Reaction notes

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