Benzyl Bromide → 4-Benzyloxy-6-fluoro-3-methyl-naphthalene-2-carboxylic acid methyl ester

HRID 238603

Reaction equation

HRID 238603 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:14]([CH3:15])=[C:13]([OH:16])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:17])[CH:11]=2)[CH:6]=1)=[O:4].C(=O)([O-])[O-].[K+].[K+].[CH2:24](Br)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>CC(C)=O>[CH3:1][O:2][C:3]([C:5]1[C:14]([CH3:15])=[C:13]([O:16][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:17])[CH:11]=2)[CH:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 593265736-Fluoro-4-hydroxy-3-methyl-naphthalene-2-carboxylic acid methyl ester

Product 1

HCID 593266024-Benzyloxy-6-fluoro-3-methyl-naphthalene-2-carboxylic acid methyl esterYield 94%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a mixture of 6-fluoro-4-hydroxy-3-methyl-naphthalene-2-carboxylic acid methyl ester (8.0 g, 34.2 mmol) and potassium carbonate (9.45 g, 68.4 mmol) was added benzyl bromide (4.5 mL, 37.6 mmol) in acetone (100 mL). The resulting mixture was vigorously stirred at reflux for 10 hours under a nitrogen atmosphere. The mixture was cooled and filtered. The combined organic solution was concentrated in vacuo to give 4-benzyloxy-6-fluoro-3-methyl-naphthalene-2-carboxylic acid methyl ester (10.4 g, 94%) as a white solid.

Workup

  1. temperatureat reflux for 10 hours under a nitrogen atmosphere
  2. temperatureThe mixture was cooled
  3. filtrationfiltered
  4. concentrationThe combined organic solution was concentrated in vacuo

Sources & evidence

ORD record
ord-fae345fd3ca24e94a92c9e1ca9a7d322
Source dataset
uspto-grants-2014_02
Patent number
US08642629B2

Linked notes

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