Benzyl Bromide → 4-Benzyloxy-6-fluoro-naphthalene-2-carboxylic acid methyl ester

HRID 1929561Notes

Reaction equation

HRID 1929561 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:14]=[C:13]([OH:15])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:16])[CH:11]=2)[CH:6]=1)=[O:4].C(=O)([O-])[O-].[K+].[K+].[CH2:23](Br)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CC(C)=O>[CH3:1][O:2][C:3]([C:5]1[CH:14]=[C:13]([O:15][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:16])[CH:11]=2)[CH:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 59326505Methyl 6-fluoro-4-hydroxy-2-naphthoate

Product 1

HCID 593265854-Benzyloxy-6-fluoro-naphthalene-2-carboxylic acid methyl esterYield 90%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a mixture of 6-fluoro-4-hydroxy-naphthalene-2-carboxylic acid methyl ester (4.6 g, 21 mmol) and potassium carbonate (5.8 g, 42 mmol), was added benzyl bromide (5.47 mL, 32 mmol) in acetone (100 mL). After being stirred vigorously at reflux for 4 hours under a nitrogen atmosphere, the resulting mixture was cooled to room temperature, filtered, and concentrated in vacuo to give 4-benzyloxy-6-fluoro-naphthalene-2-carboxylic acid methyl ester (5.85 g, 90%) as a white solid.

Workup

  1. temperatureat reflux for 4 hours under a nitrogen atmosphere
  2. filtrationfiltered
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-228d3601a6644040af15859d6fd9d6a9
Source dataset
uspto-grants-2012_05
Patent number
US08188090B2

Reaction notes

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