N-bromobutanimide → 1,1'-Biphenyl, 4'-(bromomethyl)-2-nitro-

HRID 257251

Reaction equation

HRID 257251 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=1)([O-:3])=[O:2].C1C(=O)N([Br:24])C(=O)C1>C(Cl)(Cl)(Cl)Cl.CC(N=NC(C#N)(C)C)(C#N)C>[Br:24][CH2:16][C:13]1[CH:12]=[CH:11][C:10]([C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N+:1]([O-:3])=[O:2])=[CH:15][CH:14]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 104431944'-Methyl-2-nitro-1,1'-biphenyl

Product 1

HCID 117790721,1'-Biphenyl, 4'-(bromomethyl)-2-nitro-Yield 92.1%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A solution/suspension of 3.74 g (17.5 mmol) 2-nitro-4'-methylbiphenyl, 123 mg (0.9 mmol) AIBN, and 3.43 g (19.3 mmol) NBS in 180 mL CCl4 was refluxed for 30 minutes. The mixture was cooled to room temperature, was filtered through a medium fritted funnel, was washed with water, was dried over magnesium sulfate, was stripped of solvent in vacuo, and was chromatographed on silica gel under medium pressure using 7% ethyl acetate in hexanes to give 4.71 g (92% yield) of the title compound as a light yellow crystalline solid. Rf 0.21 in 10% EtOAc/hexane, visualized by UV and ammonium molybdate/ceric sulfate stain. 1H-NMR (400 MHz, CDCl3): δ7.88 (m, 1H), 7.63 (m, 2H), 7.52 (m, 1H), 7.45 (m, 2H), 7.31 (m, 2H), 4.54 (s, 2H); a small singlet at d 6.69 (benzylic proton) is observed for for the dibrominated material.

Workup

  1. temperaturewas refluxed for 30 minutes
  2. filtrationwas filtered through a medium fritted funnel
  3. washwas washed with water
  4. dry with materialwas dried over magnesium sulfate
  5. customwas chromatographed on silica gel under medium pressure

Sources & evidence

ORD record
ord-f44271628271467999496c2925adef26
Source dataset
uspto-grants-1993_11
Patent number
US05260285

Linked notes

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