1-(Bromomethyl)-3-chlorobenzene → HCID 58017135, compound

HRID 883664Notes

Reaction equation

HRID 883664 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:10]3([CH2:14][C:13](=[O:15])[NH:12][C:11]3=[O:16])[C:9](=[O:17])[N:8]([CH2:18][C:19]([O:21][CH3:22])=[O:20])[C:5]2=[CH:6][CH:7]=1.CC(C)([O-])C.[K+].[Cl:29][C:30]1[CH:31]=[C:32]([CH:35]=[CH:36][CH:37]=1)[CH2:33]Br.O1CCCC1.C(OCC)C>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:10]3([CH2:14][C:13](=[O:15])[N:12]([CH2:33][C:32]4[CH:35]=[CH:36][CH:37]=[C:30]([Cl:29])[CH:31]=4)[C:11]3=[O:16])[C:9](=[O:17])[N:8]([CH2:18][C:19]([O:21][CH3:22])=[O:20])[C:5]2=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 698381-(Bromomethyl)-3-chlorobenzeneHCID 21868444Ether tetrahydrofuranHCID 23665647Potassium tert-butoxideHCID 58017108HCID 58017108, compound

Product 1

HCID 58017135HCID 58017135, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Following the general procedure (Route A) as outlined above for the synthesis of intermediate 16, methyl (5-chloro-2,2′,5′-trioxospiro[indole-3,3′-pyrrolidin]-1(2H)-yl)acetate, intermediate 47, (2.94 g, 9.11 mmol) was reacted with potassium tert-butoxide (1.07 g, 9.57 mmol) and 3-chlorobenzyl bromide (1.25 ml, 9.57 mmol) in anhydrous N,N-dimethylformamide (90 ml) at ambient temperature for two hours to give the title compound (2.10 g, 52%) as slightly pink powder after trituration from tetrahydrofuran/diethyl ether. The compound was isolated in several fractions (HPLC purity: 96-99%). MS (ESI+): 447.3; MS (ESI−): 445.3

Sources & evidence

ORD record
ord-cccf1b195eb343f2b4c4a9c101496cf8
Source dataset
uspto-grants-2012_08
Patent number
US08236963B2

Reaction notes

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