Sodium Carbonate → 2-Ethoxy-1-(2-fluoro-5-bromophenyl)naphthalene

HRID 539259Notes

Reaction equation

HRID 539259 reaction equation
[CH2:1]([O:3][C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]=1B(O)O)[CH3:2].[F:17][C:18]1[CH:23]=[CH:22][C:21]([Br:24])=[CH:20][C:19]=1I.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]=1[C:23]1[CH:22]=[C:21]([Br:24])[CH:20]=[CH:19][C:18]=1[F:17])[CH3:2]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 27827504-Bromo-1-fluoro-2-iodobenzeneHCID 16213801(2-Ethoxynaphthalen-1-yl)boronic acid

Product 1

HCID 677732662-Ethoxy-1-(2-fluoro-5-bromophenyl)naphthaleneYield 70%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In the atmosphere of argon, 22.7 g of 2-ethoxynaphthalene-1-boronic acid, 30.0 g of 2-fluoro-5-bromoiodobenzene, 2.31 g of tetrakistriphenylphosphine palladium (0), 300 mL of toluene and 150 mL of an aqueous 2M solution of sodium carbonate were placed in a flask, and the resulting mixture was stirred with heating under reflux for 8 hours. After cooling to room temperature, the reaction solution was extracted with toluene. An aqueous phase was removed, and then, an organic phase was washed with saturated saline. The organic phase was dried with magnesium sulfate, and concentrated. Residues were purified by means of silica gel column chromatography, whereby 24.1 g (yield: 70%) of 2-ethoxy-1-(2-fluoro-5-bromophenyl)naphthalene was obtained.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for 8 hours
  3. extractionthe reaction solution was extracted with toluene
  4. customAn aqueous phase was removed
  5. washan organic phase was washed with saturated saline
  6. dry with materialThe organic phase was dried with magnesium sulfate
  7. concentrationconcentrated
  8. customResidues were purified by means of silica gel column chromatography

Sources & evidence

ORD record
ord-607977f1f1c34210a31e5247cf806a48
Source dataset
uspto-grants-2014_10
Patent number
US08866135B2

Reaction notes

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