Water → HCID 18629362, compound

HRID 1061462Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([O:12][CH3:13])[C:5]([CH2:10]Br)=[C:6]([CH2:8]Br)[CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[C:20]([NH2:39])([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.O>CN(C=O)C>[Br:1][C:2]1[CH:7]=[C:6]2[C:5]([CH2:10][N:39]([C:20]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)([C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=3)[C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH2:8]2)=[C:4]([O:12][CH3:13])[CH:3]=1

Participants

Conditions

Temperature: 90 °C

Procedure

4.95 g of 5-bromo-1,2-bis(bromomethyl)-3-methoxybenzene (3-19) was dissolved in 150 ml of anhydrous DMF, to which 5.50 g of potassium carbonate and 4.30 g of tritylamine, and under an argon atmosphere, the resulting mixture was stirred at 90° C. for 8 hours. The reaction solution was poured into water, and extract with chloroform and the resulting organic layer was washed with saturated salt water, and thereafter, the resulting organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and thereafter, the resulting residue was recrystallized with 2-propanol to obtain 3.35 g of 6-bromo-4-methoxy-2-tritylisoindoline (3-20).

Workup

extractionextract with chloroform
washthe resulting organic layer was washed with saturated salt water
dry with materialthe resulting organic layer was dried over anhydrous magnesium sulfate
distillationThe solvent was distilled off under reduced pressure
customthe resulting residue was recrystallized with 2-propanol

Sources & evidence

ORD record: ord-5c22ef51e44e4effa1429a0f95c0d923
Source dataset: uspto-grants-2003_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06525066B2

Reaction notes

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