N-bromobutanimide → 3-bromo-2-[(2-ethylhexyl)oxy]-7H-benzo[de]anthracene-7-one

HRID 1760140Notes

Reaction equation

[CH2:1]([CH:3]([CH2:24][CH2:25][CH2:26][CH3:27])[CH2:4][O:5][C:6]1[CH:23]=[C:10]2[CH:11]=[CH:12][CH:13]=[C:14]3[C:15](=[O:22])[C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][C:21]=4[C:8](=[C:9]23)[CH:7]=1)[CH3:2].[Br:28]N1C(=O)CCC1=O>CN(C=O)C>[Br:28][C:23]1[C:6]([O:5][CH2:4][CH:3]([CH2:1][CH3:2])[CH2:24][CH2:25][CH2:26][CH3:27])=[CH:7][C:8]2[C:21]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[C:15](=[O:22])[C:14]3[C:9]=2[C:10]=1[CH:11]=[CH:12][CH:13]=3

Participants

Conditions

Temperature: 50 °C

Procedure

A 500 ml three neck round bottom flask was equipped with a mechanical stirrer, heating mantle and condenser. To the flask was added 28.5 g 2-[(2-ethylhexyl)oxy]-7H-benzo[de]anthracene-7-one, 15 g N-bromosuccinimide and 160 g DMF. The mixture was agitated well, heated to 50° C. and held at 50° C. for two hours. The mixture was cooled to 0° C. and, after several hours, the mixture was filtered to recover the solid product. The solid was suspended in 250 g water, stirred well and filtered. The yellow solid product was dried in a 50° C. oven for ten hours to give 27.1 g of 3-bromo-2-[(2-ethylhexyl)oxy]-7H-benzo[de]anthracene-7-one with melting point of 85-88° C.

Workup

temperatureheating mantle and condenser
temperatureThe mixture was cooled to 0° C. and, after several hours
filtrationthe mixture was filtered
customto recover the solid product
stirringstirred well
filtrationfiltered
customThe yellow solid product was dried in a 50° C. oven for ten hours

Sources & evidence

ORD record: ord-71947c9067954a6680e034bb3f27267a
Source dataset: uspto-grants-2005_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06841236B2

Reaction notes

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