Azobisisobutyronitrile → HCID 86712493, compound

HRID 1528561Notes

Reaction equation

[CH2:1]([O:7][C:8]1[CH:13]=[C:12]([C:14]2[O:15][C:16]3[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[C:17]=3[N:18]=2)[C:11]([O:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])=[CH:10][C:9]=1[C:31]1[O:32][C:33]2[CH:39]=[CH:38][C:37]([C:40]([CH3:43])([CH3:42])[CH3:41])=[CH:36][C:34]=2[N:35]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[Br:44]N1C(=O)CCC1=O.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[Br:44][CH2:23][C:19]1[C:17]2[N:18]=[C:14]([C:12]3[CH:13]=[C:8]([O:7][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])[C:9]([C:31]4[O:32][C:33]5[CH:39]=[CH:38][C:37]([C:40]([CH3:41])([CH3:43])[CH3:42])=[CH:36][C:34]=5[N:35]=4)=[CH:10][C:11]=3[O:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[O:15][C:16]=2[CH:22]=[CH:21][CH:20]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of 2-(2,5-bis(hexyloxy)-4-(4-methylbenzo[d]oxazol-2-yl)phenyl)-5-(tert-butyl)benzo[d]oxazol (3.7 g, 6.35 mmol), N-bromosuccinimide (NBS) (1.13 g, 6.35 mmol), and AIBN (0.1 g, 0.6 mmol) in CCl4 (40 mL) was heated to reflux for 15 h under dry argon atmosphere. The reaction mixture was cooled to 0° C. and the precipitate was removed by filtration while maintaining the temperature at 0° C. After the solvent was evaporated, 4-(bromomethyl)-2-(4-(5-(tert-butyl)benzo[d]oxazol-2-yl)-2,5-bis(hexyloxy)phenyl)benzo[d]oxazole was obtained as an oil, which was used for next step without further purification.

Workup

temperaturewas heated
temperatureto reflux for 15 h under dry argon atmosphere
customthe precipitate was removed by filtration
temperaturewhile maintaining the temperature at 0° C
customAfter the solvent was evaporated

Sources & evidence

ORD record: ord-3fb6720d529941a9a54bb7b80a96e9f9
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09090602B2

Reaction notes

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