Fluorobenzene → HCID 86594756, compound

HRID 250963Notes

Reaction equation

HRID 250963 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[Br:5][C:6]1[C:11]([C:12]2(O)[CH2:16][CH2:15][CH2:14][CH2:13]2)=[CH:10][CH:9]=[CH:8][N:7]=1.[OH-].[Na+].[F:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>>[Br:5][C:6]1[C:11]([C:12]2([C:24]3[CH:25]=[CH:26][C:21]([F:20])=[CH:22][CH:23]=3)[CH2:16][CH2:15][CH2:14][CH2:13]2)=[CH:10][CH:9]=[CH:8][N:7]=1

Participants

5

Reactant 4

HCID 10008Fluorobenzene2×HCID 14798Sodium HydroxideHCID 6451240Aluminum(III) ChlorideHCID 86594757HCID 86594757, compound

Product 1

HCID 86594756HCID 86594756, compoundYield 69%

Procedure

To a suspension of AlCl3 (4.05 g, 30.36 mmol) in fluorobenzene (10 mL) was added a solution of the 1-(2-bromo-pyridin-3-yl)-cyclopentanol (1.05 g, 4.33 mmol) in fluorobenzene (15 mL) and the resulting mixture was stirred overnight. The mixture was poured into ice (100 ml), basified with NaOH (10 N) to pH14, and extracted with EtOAc (4×40 mL). The combined organic extracts were washed with brine (2×50 mL), dried (MgSO4), filtered, and concentrated to afford a brown oil. Purification by flash column chromatography on silica gel using hexanes/EtOAc (2:1) afforded 2-bromo-3-[1-(4-fluoro-phenyl)-cyclopentyl]-pyridine as a yellow oil (956 mg, 69%).

Workup

  1. extractionextracted with EtOAc (4×40 mL)
  2. washThe combined organic extracts were washed with brine (2×50 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto afford a brown oil
  7. customPurification by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-36f5dc3a701146a2910f2425e5bda2cc
Source dataset
uspto-grants-2011_01
Patent number
US07863293B2

Reaction notes

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