Water → 4-Aminobiphenyl

HRID 661509Notes

Reaction equation

HRID 661509 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:8]1(Br)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[Mg].BrN1C(=O)CCC1=O.O>C(Cl)Cl>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6115AnilineHCID 67184N-bromobutanimideHCID 66586406HCID 66586406, compound

Product 1

HCID 71024-Aminobiphenyl

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

According to a method described in Bumagin, N. A. and Luzikova, E. V. J. Organometallic Chem. 532, 271-273(1997), 4-aminobiphenyl (18.0 g, 0.1 mol) was synthesized from 4-iode aniline and magnesium phenyl bromide and dissolved in methylene chloride (150 mL). The solution thus obtained was cooled down to 0° C. Into the solution, N-bromosuccinimide (19 g, 0.1 mol) was gradually added and stirred at the room temperature for 12 hours. After the reaction was completed, water (100 mL) was added therein to terminate the reaction. The resultant was extracted with chloroform (50 mL×3) and then washed with water (50 mL×5). The resultant was then dried with anhydrous magnesium sulfate and then distilled under reduced pressure to remove the solvent. The resultant was purified via column chromatography (silica gel, chloroform/hexane (1:1 (v/v), Rf=0.2), thereby obtaining 3-bromo-4-aminobiphenyl (compound 4) in a form of an orange-tan solid. Then, 3-bromo-4-aminobiphenyl (compound 4) was recrystallized using hexane, thereby obtaining an orange-tan needle-like crystal (17.7 g, 72%).

Workup

  1. customThe solution thus obtained
  2. customto terminate
  3. customthe reaction
  4. extractionThe resultant was extracted with chloroform (50 mL×3)
  5. washwashed with water (50 mL×5)
  6. dry with materialThe resultant was then dried with anhydrous magnesium sulfate
  7. distillationdistilled under reduced pressure
  8. customto remove the solvent
  9. customThe resultant was purified via column chromatography (silica gel, chloroform/hexane (1:1 (v/v), Rf=0.2)
  10. customThen, 3-bromo-4-aminobiphenyl (compound 4) was recrystallized

Sources & evidence

ORD record
ord-f1a085c3726a4872af3e5300798826b6
Source dataset
uspto-grants-2011_12
Patent number
US08084624B2

Reaction notes

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