Benzyl Chloride → 1-Benzyl-5-fluoro-1H-indole

HRID 5601

Reaction equation

HRID 5601 reaction equation
C1OCCOCCOCCOCCOCCOC1.CC(C)([O-])C.[K+].[F:25][C:26]1[CH:27]=[C:28]2[C:32](=[CH:33][CH:34]=1)[NH:31][CH:30]=[CH:29]2.[CH2:35](Cl)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>CCOCC.O>[CH2:35]([N:31]1[C:32]2[C:28](=[CH:27][C:26]([F:25])=[CH:34][CH:33]=2)[CH:29]=[CH:30]1)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

7

Reactant 4

HCID 7503Benzyl ChlorideHCID 2855718-Crown-6HCID 678615-FluoroindoleHCID 23665647Potassium tert-butoxide

Product 1

HCID 197966391-Benzyl-5-fluoro-1H-indoleYield 14.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent3×

Procedure

To a solution of 0.8 g (3.03 mmoles) of 18-crown-6 in 100 ml of dry ether was added 3.27 g (29.14 mmoles) of potassium tert-butoxide. The mixture was stirred while a solution of 3.75 g (27.75 mmoles) of 5-fluoroindole in 80 ml of ether was added. The stirring was continued for 0.5 hour. Solid was present. Then 3.69 g (29.15 mmoles) of benzyl chloride in 80 ml of ether was added. The mixture was stirred for 28 hours. Water (100 ml) was added. The layers were separated. The aqueous layer was extracted with 100 ml of ether. The combined ether layers were washed with 50 ml of brine and dried over MgSO4. Evaporation of the solvent left 6.95 g of orange oil. The oil was chromatographed on a 600 g column of silica gel. The column was eluted with 30% CH2Cl2 -Skellysolve B and 200 ml fractions were collected. The fractions were assayed by silica gel tlc (1×4") (30% CH2Cl1 -Skellysolve B). Fractions 11-15 were combined giving 0.88 g (14%) of 1-benzyl-5-fluoroindole as a pale yellow oil which contained a small amount of 1,3-dibenzyl-5-fluorindole.

Workup

  1. additionwas added
  2. customThe layers were separated
  3. extractionThe aqueous layer was extracted with 100 ml of ether
  4. washThe combined ether layers were washed with 50 ml of brine
  5. dry with materialdried over MgSO4
  6. customEvaporation of the solvent
  7. waitleft 6.95 g of orange oil
  8. customThe oil was chromatographed on a 600 g column of silica gel
  9. washThe column was eluted with 30% CH2Cl2 -Skellysolve B and 200 ml fractions
  10. customwere collected

Sources & evidence

ORD record
ord-d0c9152d9e564c87bc2c916dccd31853
Source dataset
uspto-grants-1993_09
Patent number
US05245046

Linked notes

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