Toluene → HCID 12104084, compound

HRID 1897397Notes

Reaction equation

HRID 1897397 reaction equation
[OH:1][C:2]([C:5]([OH:8])([CH3:7])[CH3:6])([CH3:4])[CH3:3].[CH2:9]([CH:11]([CH2:40][CH2:41][CH2:42][CH3:43])[CH2:12][C:13]1([CH2:32][CH:33]([CH2:38][CH3:39])[CH2:34][CH2:35][CH2:36][CH3:37])[C:25]2[CH:24]=[C:23]([B:26](O)O)[CH:22]=[CH:21][C:20]=2[C:19]2[C:14]1=[CH:15][C:16]([B:29]([OH:31])[OH:30])=[CH:17][CH:18]=2)[CH3:10].[CH3:44]CCCCC.ClCCl.[C:53]1([CH3:59])[CH:58]=[CH:57]C=C[CH:54]=1>>[CH3:3][C:2]1([CH3:4])[C:5]([CH3:7])([CH3:6])[O:8][B:26]([C:23]2[CH:22]=[CH:21][C:20]3[C:19]4[C:14](=[CH:15][C:16]([B:29]5[O:31][C:53]([CH3:59])([CH3:54])[C:58]([CH3:44])([CH3:57])[O:30]5)=[CH:17][CH:18]=4)[C:13]([CH2:32][CH:33]([CH2:38][CH3:39])[CH2:34][CH2:35][CH2:36][CH3:37])([CH2:12][CH:11]([CH2:9][CH3:10])[CH2:40][CH2:41][CH2:42][CH3:43])[C:25]=3[CH:24]=2)[O:1]1

Participants

6

Reactant 5

HCID 1140TolueneHCID 6344DichloromethaneHCID 6425PinacolHCID 8058HexaneHCID 3463751[9,9-Bis(2-ethylhexyl)-9H-fluorene-2,7-diyl]diboronic acid

Product 1

HCID 12104084HCID 12104084, compoundYield 37.7%

Conditions

Temperature
80 °C

Procedure

Pinacol (0.43 g, 3.66 mmol) and 9,9-di(2′-ethylhexyl)fluorene-2,7-diboronic acid (0.5 g, 1.05 mmol) were dissolved in anhydrous toluene (30 mL) and, after heating to 80° C., the mixture was stirred for 4 hours. After the reaction was terminated, the produced compound was extracted with distilled water and dichloromethane, dried with anhydrous MgSO4 and filtered under reduced pressure. The final product 2,7-bis(4,4,5,5,-tetramethyl[1.3.2]dioxaborolan-2-yl)-9,9-bis(2-ethylhexyl)-fluorene (0.28 g, yield: 37.7%) was obtained by column chromatography (n-hexane:dichloromethane=3:1). 1H NMR (300 MHz, CDCl3, ppm): δ 7.84-7.69 (m, 6H), 2.00 (d, J=5.3 Hz, 4H), 1.36 (s, 24H), 0.86-0.50 (m, 22H), 0.48-0.45 (m, 8H).

Workup

  1. customAfter the reaction was terminated
  2. extractionthe produced compound was extracted with distilled water and dichloromethane
  3. dry with materialdried with anhydrous MgSO4
  4. filtrationfiltered under reduced pressure

Sources & evidence

ORD record
ord-3120b9e3969b4aebbb85d78401055b98
Source dataset
uspto-grants-2013_08
Patent number
US08519087B2

Reaction notes

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