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

HRID 238595Notes

Reaction equation

HRID 238595 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), potassium carbonate (5.8 g, 42 mmol) and acetone (100 mL) was added benzyl bromide (5.47 g, 32 mmol). After being stirred vigorously at reflux for 4 hours under a nitrogen atmosphere, the resulting mixture was cooled to room temperature, and filtered. The organic solution was 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. concentrationThe organic solution was concentrated in vacuo

Sources & evidence

ORD record
ord-7d85ba0135d1418681074f05e1c8bfee
Source dataset
uspto-grants-2014_02
Patent number
US08642629B2

Reaction notes

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