Water → HCID 12925266, compound

HRID 1461948Notes

Reaction equation

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

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 30.9 g of 4-acetyl-4'-octylbiphenyl in 50 ml of acetic acid there are added 5.1 ml of bromine for one hour under stirring at the temperature of 50° C. The reaction mass is stirred for 1 hour at room temperature, poured into water, the organic layer is extracted with chloroform, the extract is washed with a 5% aqueous solution of soda, then with water and dried with sodium sulphate. Chloroform is distilled-off in vacuum and the residue is recrystallized from a minimum amount of ethanol to give 38 g of 4-bromoacetyl-4'-octylbiphenyl; from 19.6 g of the product and 16.5 g of benzaldehydeguanylhydrazone there is obtained, following the procedure of Example 1, 0.65 g of 1,1'-bisbenzylideneamino-4,4'-di-[4-(4-octylphenylene)-phenylene]-2,2'-azoimidazole (II /3/). The analysis data are shown in Table 1 hereinbelow.

Workup

stirringThe reaction mass is stirred for 1 hour at room temperature
extractionthe organic layer is extracted with chloroform
washthe extract is washed with a 5% aqueous solution of soda
dry with materialwith water and dried with sodium sulphate
customthe residue is recrystallized from a minimum amount of ethanol

Sources & evidence

ORD record: ord-2b101edcea4f4032b5fd21041ca0de65
Source dataset: uspto-grants-1984_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04457859

Reaction notes

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