Potassium hydroxide ethanol → 5-Bromo-2-(7-bromo-9,9'-Dioctyl-9H-fluoren-2-yl)benzoic acid

HRID 596137Notes

Reaction equation

HRID 596137 reaction equation
C[O:2][C:3](=[O:41])[C:4]1[CH:9]=[C:8]([Br:10])[CH:7]=[CH:6][C:5]=1[C:11]1[CH:23]=[CH:22][C:21]2[C:20]3[C:15](=[CH:16][C:17]([Br:24])=[CH:18][CH:19]=3)[C:14]([CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[C:13]=2[CH:12]=1.[OH-].[K+].C(O)C>C(O)C>[Br:10][C:8]1[CH:7]=[CH:6][C:5]([C:11]2[CH:23]=[CH:22][C:21]3[C:20]4[C:15](=[CH:16][C:17]([Br:24])=[CH:18][CH:19]=4)[C:14]([CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[C:13]=3[CH:12]=2)=[C:4]([CH:9]=1)[C:3]([OH:41])=[O:2]

Participants

4

Reactant 2

HCID 21946426Potassium hydroxide ethanolHCID 867235505-Bromo-2-(7-bromo-9,9'-Dioctyl-9H-fluoren-2-yl)benzoic acid methyl ester

Product 1

HCID 586075385-Bromo-2-(7-bromo-9,9'-Dioctyl-9H-fluoren-2-yl)benzoic acidYield 102.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

35 g (51.2 mmol) 16 is suspended in 300 ml ethanol and treated with 50 ml 50% KOH/ethanol solution and heated to reflux for 3 h. After cooling to room temperature with reaction mixture is diluted with 200 ml ethanol, with precipitation is collected by filtration, the residue is washed with ethanol and dried in vacuum. 35 g (yield: 98%) of a white solid can be obtained.

Workup

  1. temperatureheated
  2. temperatureto reflux for 3 h
  3. filtrationis collected by filtration
  4. washthe residue is washed with ethanol
  5. customdried in vacuum

Sources & evidence

ORD record
ord-563a2223e3b2475a85831acdb2feaa2f
Source dataset
uspto-grants-2016_01
Patent number
US09246103B2

Reaction notes

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