4-Bromobiphenyl → HCID 9817140, compound

HRID 481996Notes

Reaction equation

HRID 481996 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.[Mg].[N:15]12[CH2:22][CH2:21][CH:18]([CH2:19][CH2:20]1)[C:17](=[O:23])[CH2:16]2.[Cl-].[NH4+]>O1CCCC1.BrBr>[C:5]1([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:7][C:2]([C:17]2([OH:23])[CH:18]3[CH2:21][CH2:22][N:15]([CH2:20][CH2:19]3)[CH2:16]2)=[CH:3][CH:4]=1

Participants

7

Reactant 4

HCID 71014-BromobiphenylHCID 195073-QuinuclidinoneHCID 25517Ammonium ChlorideHCID 5462224Magnesium

Product 1

HCID 9817140HCID 9817140, compoundYield 17.2%

Reagents, catalysts & solvents 2

HCID 24408BromineCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 4-bromobiphenyl (11.8 g) in dry tetrahydrofuran (60 ml) and bromine (3 drops) were added to stirred magnesium turnings (1.18 g) and the mixture heated under reflux for 70 minutes. A solution of quinuclidin-3-one (3.65 g) in dry tetrahydrofuran (25 ml) was added dropwise to the mixture at 10° C. and the reaction mixture heated under reflux for 90 minutes. Aqueous ammonium chloride (14 g in 56 ml of water) was added dropwise to the mixture and the mixture extracted with diethyl ether. The ether extract was dried (Na2SO4) and evaporated to give a residue which was crystallised from ethyl acetate to give 3-(biphenyl-4-yl)-3-hydroxyquinuclidine (1.4 g) as a colourless solid, m.p. 180°-182° C., microanalysis, found: C, 81.7; H, 7.5; N, 5.0%; C19H21NO requires: C, 81.8; H, 7.5; N, 5.0%. This material was identical to that in Example 1 except that it was a higher melting polymorphic form.

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux for 70 minutes
  3. temperaturethe reaction mixture heated
  4. temperatureunder reflux for 90 minutes
  5. extractionthe mixture extracted with diethyl ether
  6. extractionThe ether extract
  7. dry with materialwas dried (Na2SO4)
  8. customevaporated
  9. customto give a residue which
  10. customwas crystallised from ethyl acetate

Sources & evidence

ORD record
ord-2d098a25a12548e78ec27014bbc09348
Source dataset
uspto-grants-1998_08
Patent number
US05792777

Reaction notes

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