1,2-Dibromobenzene → 1,4-Bis(anthracen-9-yl)naphthalene

HRID 1190237

Reaction equation

HRID 1190237 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1Br.Br[C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13](Br)=[CH:12][CH:11]=1.[CH:21]1[C:34]2[C:25](=[CH:26][C:27]3[C:32]([C:33]=2B(O)O)=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH:24]=[CH:23][CH:22]=1>>[CH:4]1[C:3]2[C:2](=[CH:15][C:14]3[C:19]([C:18]=2[C:10]2[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[C:13]([C:33]4[C:34]5[C:25]([CH:26]=[C:27]6[C:32]=4[CH:31]=[CH:30][CH:29]=[CH:28]6)=[CH:24][CH:23]=[CH:22][CH:21]=5)=[CH:12][CH:11]=2)=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 3

HCID 114141,2-DibromobenzeneHCID 665211,4-DibromonaphthaleneHCID 155102139-Anthraceneboronic Acid

Product 1

HCID 591334251,4-Bis(anthracen-9-yl)naphthalene

Procedure

Procedure analogous to Example 3a. Instead of 149.0 ml (1.2 mol) of 1,2-dibromobenzene and 98.0 g (308 mmol) of 9,10-anthracenediboronic acid ethylene glycol ester, 28.6 g (100 mmol) of 1,4-dibromonaphthalene and 68.0 g (306 mmol) of 9-anthraceneboronic acid are used. After cooling, the solid is filtered off with suction and washed twice with 500 ml of boiling ethanol each time. Yield: 33.0 g (69 mmol), 68.7% of theory; purity: 98% according to 1H-NMR.

Workup

  1. temperatureAfter cooling
  2. filtrationthe solid is filtered off with suction
  3. washwashed twice with 500 ml of boiling ethanol each time

Sources & evidence

ORD record
ord-7f37cb8c35414d9daf1baae32eec3e51
Source dataset
uspto-grants-2014_03
Patent number
US08674141B2

Linked notes

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