4-Bromobiphenyl → HCID 18328732, compound

HRID 1249683Notes

Reaction equation

HRID 1249683 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.[NH:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1.CC(C)([O-])C.[Na+].O.C(OCC)(=O)C>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]([N:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)=[CH:3][CH:4]=1

Participants

6

Reactant 4

HCID 71014-BromobiphenylHCID 31268PyrrolidineHCID 22728543Water ethylacetateHCID 23676156Sodium t-butoxide

Product 1

HCID 18328732HCID 18328732, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

10.0 g (0.043 mol) of 4-bromobiphenyl were suspended in 600 ml of toluene together with 3.7 g (0.052 mol) of pyrrolidine and 6.2 g (0.0642 mol) of sodium tertiary-butoxide and 900 mg of the catalyst dichlorobis(tritolylphosphine)palladium(II) were added. The mixture was heated to reflux for 8 h, cooled, treated with water/ethyl acetate, and the organic phase was washed with water, dried over sodium sulfate and concentrated. The residue was dissolved in approximately 300 ml of tertiary-butyl methyl ether and the hydrochloride of the product was precipitated by addition of 50 ml of 1N ethereal HCl.

Workup

  1. additionwere added
  2. temperatureThe mixture was heated
  3. temperatureto reflux for 8 h
  4. temperaturecooled
  5. washthe organic phase was washed with water
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. dissolutionThe residue was dissolved in approximately 300 ml of tertiary-butyl methyl ether
  9. customthe hydrochloride of the product was precipitated by addition of 50 ml of 1N ethereal HCl

Sources & evidence

ORD record
ord-ac566f187c4d4dec89d6f6a8b867ef7b
Source dataset
uspto-grants-2002_01
Patent number
US06335333B1

Reaction notes

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