Dimethylformamide → 2-Methoxy-7-phenylnaphthalene

HRID 1476364Notes

Reaction equation

HRID 1476364 reaction equation
P([O-])([O-])([O-])=O.[K+].[K+].[K+].[C:9]1(OB(O)O)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[Cl-].[NH4+].CN([CH:24]=[O:25])C>>[C:9]1([C:9]2[CH:14]=[C:13]3[C:12]([CH:14]=[CH:9][C:10]([O:25][CH3:24])=[CH:11]3)=[CH:11][CH:10]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 62657Potassium Phosphate, TribasicHCID 78412Phenyl dihydrogen orthoborate

Product 1

HCID 220481542-Methoxy-7-phenylnaphthaleneYield 73%

Conditions

Temperature
80 °C

Procedure

n-Hydrate of potassium phosphate (34 g, 0.16 mol) and phenylboric acid (3.7 g, 30 mmol) were added to a DMF (350 ml) solution of 7-methoxy-2-naphthyltrifluoromethane sulfonate (6.1 g, 20 mmol). The solution was bubbled with nitrogen for 30 minutes to perform replacement with nitrogen. PdCl2(PPh)2 (0.71 g, 1 mmol) was added, and the solution was heated for 4 hours at 80° C. A saturated ammonium chloride aqueous solution (500 ml) was added to the obtained mixture. Crystals deposited by this operation was filtered out, washed with water (100 ml×3), and dried with an electric dryer (60° C.). The crude product was refined by column chromatography (silica gel, developed with dichloromethane) to obtain 7-phenyl-2-methoxynaphthalene (compound (3)-22), 3.4 g).

Workup

  1. customThe solution was bubbled with nitrogen for 30 minutes
  2. filtrationwas filtered out
  3. washwashed with water (100 ml×3)
  4. customdried with an electric dryer (60° C.)

Sources & evidence

ORD record
ord-62cc30e26ec54130bc4a15c40298c03a
Source dataset
uspto-grants-2015_04
Patent number
US09018630B2

Reaction notes

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