1-Bromo-4-fluorobenzene → HCID 86754393, compound

HRID 1584802Notes

Reaction equation

HRID 1584802 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][CH:3]=1.[Mg].C([O:12][C:13]([CH:15]1[CH2:20][CH2:19][N:18]([C:21]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:17][CH2:16]1)=O)C>CCOCC.O1CCCC1>[F:8][C:5]1[CH:6]=[CH:7][C:2]([CH:19]2[CH2:20][CH:15]([CH2:13][OH:12])[CH2:16][CH2:17][N:18]2[C:21]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[CH:3][CH:4]=1

Participants

6

Reactant 3

HCID 99931-Bromo-4-fluorobenzeneHCID 5462224MagnesiumHCID 12851303HCID 12851303, compound

Product 1

HCID 86754393HCID 86754393, compoundYield 66.9%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

1-Bromo4-fluorobenzene (154 ml; 1.402 mol) in anhydrous ether (640 ml) was added to a suspension of magnesium turnings (34.1 g; 1.404 mol) in anhydrous ether (250 ml) and the mixture was stirred under nitrogen, at a rate which gave a gentle reflux. The solution was cooled, stirred at room temperature for 45 min and then cooled in an ice bath. To this solution was added dropwise over 40 min. a solution of 1-(triphenylmethyl)-4-piperidinecarboxylic acid ethylester (90 g; 0.225 mol) in anhydrous tetrahydrofuran (1.2 l). After 1 h the cooling bath was removed and the reaction was allowed to stand at room temperature overnight. The reaction mixture was then heated under reflux for 30 min, poured into ice-water and the product was extracted into ethyl acetate. The extract was filtered to remove insolubles, washed with water, dried over sodium sulfate and evaporated to yield an oil which on trituration with hot n-hexane gave the product as crystals (68.0 g); m.p. 243° C.

Workup

  1. customgave a gentle reflux
  2. temperatureThe solution was cooled
  3. stirringstirred at room temperature for 45 min
  4. temperaturecooled in an ice bath
  5. customAfter 1 h the cooling bath was removed
  6. temperatureThe reaction mixture was then heated
  7. temperatureunder reflux for 30 min
  8. additionpoured into ice-water
  9. extractionthe product was extracted into ethyl acetate
  10. filtrationThe extract was filtered
  11. customto remove insolubles
  12. washwashed with water
  13. dry with materialdried over sodium sulfate
  14. customevaporated
  15. customto yield an oil which on trituration with hot n-hexane

Sources & evidence

ORD record
ord-df924d5a5e3e4242a306f448d7e46a43
Source dataset
uspto-grants-1999_08
Patent number
US05935974

Reaction notes

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