Toluene → 6-(3,4-Difluorophenyl)-2-naphthol

HRID 992187Notes

Reaction equation

HRID 992187 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([OH:12])[CH:6]=[CH:5]2.[F:13][C:14]1[CH:15]=[C:16](OB(O)O)[CH:17]=[CH:18][C:19]=1[F:20].C1(C)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(O)C>[F:13][C:14]1[CH:15]=[C:16]([C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[CH:8]=[C:7]([OH:12])[CH:6]=[CH:5]3)[CH:17]=[CH:18][C:19]=1[F:20]

Participants

7

Reactant 4

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 271446-Bromo-2-naphthalenolHCID 218696723,4-Difluorophenylboric acid

Product 1

HCID 218708206-(3,4-Difluorophenyl)-2-naphtholYield 88.1%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolvent

Procedure

To 25.0 g of 6-bromo-2-naphthol and 22.0 g of 3,4-difluorophenylboric acid were added 100 ml of toluene, 50 ml of ethanol, 50 ml of a 2 N aqueous solution of potassium carbonate and 1.3 g of tetrakis(triphenylphosphine)palladium (0). The reaction mixture was heated under reflux for 3 hours. The reaction solution was then allowed to cool to room temperature. The resulting organic phase was separated, washed with water and saturated brine, and then dried over anhydrous sodium sulfate. The solvent was then distilled off. The residue was purified through silica gel column chromatography (dichloromethane) to obtain 25.3 g of 6-(3,4-difluorophenyl)-2-naphthol.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 3 hours
  3. customThe resulting organic phase was separated
  4. washwashed with water and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was then distilled off
  7. customThe residue was purified through silica gel column chromatography (dichloromethane)

Sources & evidence

ORD record
ord-49778d7a77264410acd17cf44f6a8f6c
Source dataset
uspto-grants-2002_10
Patent number
US06468607B1

Reaction notes

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