1-Chloro-4-(chloromethyl)benzene → HCID 70565216, compound

HRID 1477841Notes

Reaction equation

HRID 1477841 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH2:11])[C:5]2[CH:6]=[CH:7][NH:8][C:9]=2[CH:10]=1.[Cl:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17]Cl)=[CH:15][CH:14]=1.[OH-].[Na+]>>[Cl:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17][N:8]2[C:9]3[CH:10]=[C:2]([F:1])[CH:3]=[C:4]([NH2:11])[C:5]=3[CH:6]=[CH:7]2)=[CH:15][CH:14]=1

Participants

4

Reactant 3

HCID 77231-Chloro-4-(chloromethyl)benzeneHCID 14798Sodium HydroxideHCID 247280226-Fluoro-1H-indol-4-amine

Product 1

HCID 70565216HCID 70565216, compound

Conditions

Temperature
60 °C

Procedure

A mixture of 6-fluoro-1H-indol-4-amine (5 g, 0.033 mol), 4-chlorobenzyl chloride (5.55 g, 0.035 mol) and sodium hydroxide (1.32 g, 0.033 mol) was heated at 60° C. for 3 h. The solvent was evaporated and the residue was dissolved in EA (150 mL) and water (70 mL). The aqueous layer was extracted with EA and washed with brine (100 mL), dried over sodium sulfate and concentrated in vacuo. The residue was purified by silica gel flash chromatography (PE: EA=8:1) to afford the title compound. LC/MS m/z=275.1 [M+H]+.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in EA (150 mL)
  3. extractionThe aqueous layer was extracted with EA
  4. washwashed with brine (100 mL)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel flash chromatography (PE: EA=8:1)

Sources & evidence

ORD record
ord-1845c20d71304b74aec59016c3a6c9ff
Source dataset
uspto-grants-2016_08
Patent number
US09403807B2

Reaction notes

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