N-bromobutanimide → HCID 59596300, compound

HRID 2264714Notes

Reaction equation

HRID 2264714 reaction equation
[C:1]([O:5][C:6](=[O:40])[NH:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([C:25]2[CH:26]=[C:27](C3C=CC=C(OC)C=3)[C:28]([OH:31])=[CH:29][CH:30]=2)([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)[N:9]=1)([CH3:4])([CH3:3])[CH3:2].[Br:41]N1C(=O)CCC1=O>C(Cl)(Cl)Cl>[C:1]([O:5][C:6](=[O:40])[NH:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([C:25]2[CH:30]=[CH:29][C:28]([OH:31])=[C:27]([Br:41])[CH:26]=2)([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)[N:9]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 59596239HCID 59596239, compound

Product 1

HCID 59596300HCID 59596300, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To an ice cold solution of [3-(4-hydroxy-phenyl)-3-(4-methoxy-phenyl)-3H-isoindol-1-yl]-carbamic acid tert-butyl ester (Scheme #2, D) (663 mg, 1.540 mmol) in dry chloroform was added N-bromosuccinimide (274 mg, 1.540 mmol) portion-wise over 30 minutes and the reaction stirred for 25 minutes. The solvent was removed under reduced pressure and the mixture chromatographed on 80 g silica eluting with 5% acetone in dichloromethane.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe mixture chromatographed on 80 g silica eluting with 5% acetone in dichloromethane

Sources & evidence

ORD record
ord-1b4399ca5cc34ed4bad2f4007bac1920
Source dataset
uspto-grants-2010_12
Patent number
US07855213B2

Reaction notes

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