Ethanol → HCID 68555790, compound

HRID 656847Notes

Reaction equation

HRID 656847 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7](O)[CH:6]=[CH:5]2.[CH2:13](O)[CH3:14].[C:16](=[O:19])([O-])[O-].[Na+].[Na+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>[C:9]1([C:10]2[CH:11]=[CH:14][C:13]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[C:16]=2[OH:19])[C:4]2[CH2:3][C:2]3[C:10](=[CH:11][CH:2]=[CH:3][CH:4]=3)[C:5]=2[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 10340Sodium CarbonateHCID 271446-Bromo-2-naphthalenol

Product 1

HCID 68555790HCID 68555790, compoundYield 82.5%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolvent2×

Procedure

In a reaction vessel, 3.17 g (14.2 mmol) of 6-bromo-2-naphthol, 5.00 g (15.6 mmol) of 2-(9,9-dimethyl-9H-fluoren-2-yl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborane, 96.0 ml of ethanol, 6.78 g (21.3 mmol) of sodium carbonate, 48.0 ml of water, and 30 mg (14.2×10−3 mmol) of Pd(PPh3)2Cl2 were charged. Then, the resultant mixture was stirred under reflux for 4 hours and cooled. Then, water was poured to the mixture, and the mixture was filtered to produce crude crystals. The resulting crude crystals were washed with water and heptane to produce 3.94 g of fluorenylnaphthol in a yield of 82.5%.

Workup

  1. temperatureunder reflux for 4 hours
  2. temperaturecooled
  3. filtrationthe mixture was filtered
  4. customto produce crude crystals
  5. washThe resulting crude crystals were washed with water and heptane

Sources & evidence

ORD record
ord-e77feb364e06443f9acdadd95b19f7eb
Source dataset
uspto-grants-2011_12
Patent number
US08071993B2

Reaction notes

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