Water → HCID 11100222, compound

HRID 1066795Notes

Reaction equation

HRID 1066795 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][C:5]([O:6][CH2:7][C:8]2[N:9]([CH3:17])[C:10]3[C:15]([CH:16]=2)=[CH:14][CH:13]=[CH:12][CH:11]=3)=[CH:4][CH:3]=1.[Br:20]N1C(=O)CCC1=O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[Br:20][C:16]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]([CH3:17])[C:8]=1[CH2:7][O:6][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24436Sodium SulfateHCID 67184N-bromobutanimideHCID 211959852-[(4-Chlorophenoxy)methyl]-1-methyl-1H-indole

Product 1

HCID 11100222HCID 11100222, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under an argon atmosphere in a round bottom flask 2-[(4-chlorophenoxy)methyl]-1-methyl-1H-indole (5.0 g, 18.40 mmol) was dissolved in 46 ml of tetrahydrofuran. To this solution was added N-bromosuccinimide (3.28 g, 18.4 mmol of a freshly recrystallized lot), dissolved in 46 ml of tetrahydrofuran. The resulting mixture was stirred over an ice bath for about 3.5 hours, after which time the reaction mixture was poured into about 500 ml of water in which 5.0 grams of sodium sulfate had been dissolved.

Workup

  1. dissolutionhad been dissolved

Sources & evidence

ORD record
ord-160bd7c577f34859af237dd36e8f8f12
Source dataset
uspto-grants-2001_06
Patent number
US06245761B1

Reaction notes

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