4-Bromobiphenyl → HCID 58400034, compound

HRID 537658Notes

Reaction equation

HRID 537658 reaction equation
Br[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.[C:14]1([NH:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[NH2:27])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.CC(C)([O-])C.[Na+]>CC([O-])=O.CC([O-])=O.[Pd+2].C1(C)C=CC=CC=1>[C:5]1([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:7][C:2]([NH:27][C:22]2[C:21]([NH:20][C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:3][CH:4]=1

Participants

6

Reactant 3

HCID 71014-BromobiphenylHCID 68297N-Phenyl-o-phenylenediamineHCID 23676156Sodium t-butoxide

Product 1

HCID 58400034HCID 58400034, compoundYield 87.5%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Procedure

0.35 g (1.58 mmol) of Pd(OAc)2 and 4.8 ml (4.86 mmol) of tri-tent-butyl-phosphine (1 M solution in toluene) are added to 660 ml of degassed toluene, and the mixture is stirred for 5 min. 37.2 g (160 mmol) of 4-bromobiphenyl, 29.4 g (160 mmol) of N-phenyl-o-phenylenediamine and 22.4 g (233 mmol) of sodium tert-butoxide are then added to the solution, which is then degassed and stirred for 10 h at 140° C. under a protective-gas atmosphere. After the solution has cooled, 200 ml of NH4Cl solution and 50 ml of ethyl acetate are added, the phases are separated, washed with water, dried over MgSO4 and evaporated. The solid is dissolved in toluene and filtered off via Celite. The crude product is washed by stirring with hot heptane and washed with MeOH, giving 47 g (140 mmol) of a crystalline solid. The overall yield is 80%.

Workup

  1. customis then degassed
  2. stirringstirred for 10 h at 140° C. under a protective-gas atmosphere
  3. temperatureAfter the solution has cooled
  4. addition200 ml of NH4Cl solution and 50 ml of ethyl acetate are added
  5. customthe phases are separated
  6. washwashed with water
  7. dry with materialdried over MgSO4
  8. customevaporated
  9. dissolutionThe solid is dissolved in toluene
  10. filtrationfiltered off via Celite
  11. washThe crude product is washed
  12. stirringby stirring with hot heptane
  13. washwashed with MeOH

Sources & evidence

ORD record
ord-fafc0dadf22a4368b986a9685c4ba4a8
Source dataset
uspto-grants-2014_10
Patent number
US08865321B2

Reaction notes

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