4,4'-Dibromobiphenyl → HCID 86712050, compound

HRID 1755520Notes

Reaction equation

HRID 1755520 reaction equation
[C:1]1([NH:7][C:8]2[CH:17]=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:30]=[CH:29][C:28]([Br:31])=[CH:27][CH:26]=2)=[CH:21][CH:20]=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[Br:31][C:28]1[CH:29]=[CH:30][C:25]([C:22]2[CH:23]=[CH:24][C:19]([N:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[C:8]3[CH:17]=[CH:16][C:15]4[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=4)[CH:9]=3)=[CH:20][CH:21]=2)=[CH:26][CH:27]=1

Participants

6

Reactant 3

HCID 71104,4'-DibromobiphenylHCID 8679N-phenyl-2-naphthylamine2×HCID 23676156Sodium t-butoxide

Product 1

HCID 86712050HCID 86712050, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of N-phenylnaphthalen-2-amine (Compound 20) (5.0 g, 22.8 mmol), 4,4′-dibromobiphenyl (17.8 g, 57 mmol), Pd(dppf)Cl2 (0.73 g, 1 mmol) and sodium tert-butoxide (2.4 g, 25 mmol) in toluene (250 mL) was degassed and heated at 80° C. overnight. The whole was poured into ethyl acetate (250 mL), washed with brine, dried over Na2SO4, loaded on silica gel and purified by flash column (hexanes to hexanes/dichloromethane 9:1). The desired fraction was collected, and concentrated. The resulting solid was filtered, and washed with methanol to give a white solid (Compound 21) (6.15 g, in 60% yield).

Workup

  1. customwas degassed
  2. additionThe whole was poured into ethyl acetate (250 mL)
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. custompurified by flash column (hexanes to hexanes/dichloromethane 9:1)
  6. customThe desired fraction was collected
  7. concentrationconcentrated
  8. filtrationThe resulting solid was filtered
  9. washwashed with methanol

Sources & evidence

ORD record
ord-4644747962fe424eb9b13c33cd93490d
Source dataset
uspto-grants-2015_10
Patent number
US09172051B2

Reaction notes

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