1-Bromo-4-fluorobenzene → alpha-(4-Bromobutyl)-4-fluoro-alpha-(4-fluorophenyl)benzenemethanol

HRID 1073167Notes

Reaction equation

HRID 1073167 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][CH:3]=1.[Mg].[Br:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([O:17]CC)=O.[Cl-].[NH4+]>O(CC)CC>[Br:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][CH:3]=1)([C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][CH:3]=1)[OH:17]

Participants

6

Reactant 4

HCID 99931-Bromo-4-fluorobenzeneHCID 25517Ammonium ChlorideHCID 84580Ethyl 5-bromovalerateHCID 5462224Magnesium

Product 1

HCID 14722555alpha-(4-Bromobutyl)-4-fluoro-alpha-(4-fluorophenyl)benzenemethanol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a stirred and refluxing Grignard complex previously prepared starting from 280 parts of 1-bromo-4-fluorobenzene, 34.6 parts of magnesium and 392 parts of 1,1'-oxybisethane, was added dropwise a solution of 116 parts of ethyl 5-bromopentanoate in 392 parts of 1,1'-oxybisethane. Upon complete addition, stirring was continued for 4 hours at reflux temperature. The reaction mixture was decomposed with a saturated ammonium chloride solution and the product was extracted with 1,1'-oxybisethane. The extract was dried, filtered and evaporated. The residue was triturated in hexane. The latter was decanted and the residue was crystallized from hexane. The product was filtered off and dried at room temperature, yielding 100 parts of α-(4-bromobutyl)-4-fluoro-α-(4-fluorophenyl)benzenemethanol; mp. 55° C. (int. 49).

Workup

  1. temperaturerefluxing Grignard complex
  2. custompreviously prepared
  3. additionUpon complete addition
  4. stirringstirring
  5. temperatureat reflux temperature
  6. extractionthe product was extracted with 1,1'-oxybisethane
  7. customThe extract was dried
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue was triturated in hexane
  11. customThe latter was decanted
  12. customthe residue was crystallized from hexane
  13. filtrationThe product was filtered off
  14. customdried at room temperature

Sources & evidence

ORD record
ord-c9fc5c6731a5448d9140a3cf604f3e37
Source dataset
uspto-grants-1990_11
Patent number
US04968684

Reaction notes

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