Hydrochloric Acid → 5-Chloro-1-(4-fluorophenyl)-1H-indole

HRID 1250031Notes

Reaction equation

HRID 1250031 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([Cl:17])=[CH:14][CH:15]=3)[C:10](OC(=O)C)=[CH:9]2)=[CH:4][CH:3]=1.[BH4-].[Na+].Cl.O>CCO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([Cl:17])=[CH:14][CH:15]=3)[CH:10]=[CH:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 4311764Sodium borohydrideHCID 109247145-Chloro-1-(4-fluorophenyl)-1H-indol-3-yl acetate

Product 1

HCID 102361885-Chloro-1-(4-fluorophenyl)-1H-indole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-(4-flourophenyl)-3-acetoxy-5-chloroindole (100.0 g, 0.33 mol) was dissolved in 1000 mL EtOH. During the next hour sodium borohydride pellets (18.7 g, 1.5 eq.) were added batchwise at reflux. The reaction mixture was stirred over night at reflux and cooled to room temperature. Concentrated HCl (appr. 50 mL until pH 1) was added and the reaction mixture was stirred at room temperature for 1 hour. 200 mL demineralized water was added, and the resulting suspension was filtrated. The filter cake was washed with further 50 mL water and 10 mL EtOH. The product was dried over night in vacuum at 50° C.

Workup

  1. temperatureat reflux
  2. temperatureat reflux
  3. stirringthe reaction mixture was stirred at room temperature for 1 hour
  4. additionwas added
  5. filtrationthe resulting suspension was filtrated
  6. washThe filter cake was washed with further 50 mL water and 10 mL EtOH
  7. customThe product was dried over night in vacuum at 50° C.

Sources & evidence

ORD record
ord-e395ac259c25496d9df308b94b7242bd
Source dataset
uspto-grants-2002_01
Patent number
US06335463B1

Reaction notes

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