Hydrochloric Acid → HCID 59799424, compound

HRID 1095429Notes

Reaction equation

HRID 1095429 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[Cl:5][CH2:6][CH2:7][CH2:8][C:9](Cl)=[O:10].[F:12][C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[NH:18][CH:17]=[CH:16]2.Cl>ClCCl>[Cl:5][CH2:6][CH2:7][CH2:8][C:9]([C:16]1[C:15]2[C:19](=[CH:20][CH:21]=[C:13]([F:12])[CH:14]=2)[NH:18][CH:17]=1)=[O:10]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 678615-FluoroindoleHCID 783704-Chlorobutyryl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 59799424HCID 59799424, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a magnetically stirred mixture of AlCl3 (25 g, 0.19 mol) in dichloromethane, 4-chloro-butyryl chloride (21 ml, 0.19 mol) was slowly added at 0° C. The resulting mixture was stirred for 30 minutes and 5-fluoro-1H-indole (25 g, 0.19 mol) was slowly added. After stirring for another 30 minutes the formed orange mixture was poured onto concentrated hydrochloric acid (140 ml) and ice (200 ml) to give a pink precipitate. The precipitate was collected by filtration to give pink 4-chloro-1-(5-fluoro-1H-indol-3-yl)-butan-1-one (29 gram, 65% yield). 1H-NMR (400 MHz, DMSO-d6) δ 2.09 (quintet, J=7, 2H), 3.02 (t, J=7, 2H), 3.70 (t, J=7, 2H), 7.07 (dt, J˜9 and 2, 1H), 7.49 (dd, J˜9 and 4, 1H), 7.85 (dd, J˜9 and 2, 1H), 8.41 (d, J˜3, 1H), 12.21 (br s, 1H).

Workup

  1. additionwas slowly added at 0° C
  2. stirringAfter stirring for another 30 minutes the formed orange mixture
  3. customto give a pink precipitate
  4. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-ac3ba539b4634b42b31f2e2aff6661b4
Source dataset
uspto-grants-2012_03
Patent number
US08138174B2

Reaction notes

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