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

HRID 1478972Notes

Reaction equation

HRID 1478972 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1Br.[CH:9]1[C:22]2[C:13](=[CH:14][C:15]3[C:20]([C:21]=2B(O)O)=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:12]=[CH:11][CH:10]=1>>[CH:9]1[C:22]2[C:13](=[CH:14][C:15]3[C:20]([C:21]=2[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[C:14]2[C:15]4[C:20]([CH:21]=[C:22]5[C:13]=2[CH:12]=[CH:11][CH:10]=[CH:9]5)=[CH:19][CH:18]=[CH:17][CH:16]=4)=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:12]=[CH:11][CH:10]=1

Participants

3

Reactant 2

HCID 114141,2-Dibromobenzene2×HCID 155102139-Anthraceneboronic Acid

Product 1

HCID 577025121,2-Bis(anthracen-9-yl)benzene

Conditions

Temperature
90 °C

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, 12.1 ml (100 mmol) of dibromobenzene and 68.0 g (306 mmol) of 9-anthraceneboronic acid are used. After cooling, the solid is filtered off with suction, washed three times with 100 ml of ethanol each time and then washed twice by stirring with 1000 ml of refluxing acetic acid each time (1 h) and each time filtered off with suction after cooling to 90° C. The mother liquor is discarded in each case. The solid is finally washed once with boiling ethanol. Yield: 33.0 g (76 mmol), 76.6% of theory; purity: 98% according to 1H-NMR.

Workup

  1. temperatureAfter cooling
  2. filtrationthe solid is filtered off with suction
  3. washwashed three times with 100 ml of ethanol each time
  4. washwashed twice
  5. filtrationeach time filtered off with suction
  6. washThe solid is finally washed once with boiling ethanol

Sources & evidence

ORD record
ord-53d1fdce96dd4a84bed53a9df52b0075
Source dataset
uspto-grants-2016_08
Patent number
US09403849B2

Reaction notes

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