1-Bromo-2-naphthol → 1-(3-Chloro-2-fluorophenyl)-2-naphthol

HRID 1530739Notes

Reaction equation

HRID 1530739 reaction equation
Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[OH:12].[Cl:13][C:14]1[C:15]([F:23])=[C:16](B(O)O)[CH:17]=[CH:18][CH:19]=1.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(=O)([O-])[O-].[K+].[K+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(O)C.C1(C)C=CC=CC=1>[Cl:13][C:14]1[C:15]([F:23])=[C:16]([C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH:5]=[CH:4][C:3]=2[OH:12])[CH:17]=[CH:18][CH:19]=1

Participants

8

Reactant 4

HCID 113161-Bromo-2-naphtholHCID 11430Potassium CarbonateHCID 80271Tri-o-tolylphosphineHCID 162171583-Chloro-2-fluorophenylboronic Acid

Product 1

HCID 867176881-(3-Chloro-2-fluorophenyl)-2-naphthol

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

Into a 200 mL three-neck flask were put 5.8 g (26 mmol) of 1-bromo-2-naphthol, 4.5 g (26 mmol) of 3-chloro-2-fluorobenzeneboronic acid, and 0.40 g (1.3 mol) of tri(ortho-tolyl)phosphine, and the air in the flask was replaced with nitrogen. To this mixture were added 150 mL of toluene, 50 mL of ethanol, and 21 mL of an aqueous solution of potassium carbonate (2.0 mol/L). The mixture was degassed by being stirred while the pressure in the flask was reduced, and then the air in the flask was replaced with nitrogen. To this mixture was added 58 mg (0.26 mmol) of palladium(II) acetate, and the resulting mixture was stirred at 90° C. under a nitrogen stream for 7 hours.

Workup

  1. customInto a 200 mL three-neck flask were put
  2. customThe mixture was degassed
  3. stirringthe resulting mixture was stirred at 90° C. under a nitrogen stream for 7 hours

Sources & evidence

ORD record
ord-1aa2b727bc634af380bda99e2bc45a4c
Source dataset
uspto-grants-2015_07
Patent number
US09093649B2

Reaction notes

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